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Acetic Acid → 2-((3-(1-Carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylamino)methyl)-5-methylbenzoic acid

HRID 2361340
Notes
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Reaction equation

HRID 2361340 reaction equation
[NH2:1][C:2]1[C:3]([F:29])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][C:16]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:17][CH:18]=4)[NH:13][C:12]=3[C:11]([C:26]([NH2:28])=[O:27])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:30]([C:32]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:33]=1[C:34]([OH:36])=[O:35])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C1COCC1.O.CCOC(C)=O>[C:26]([C:11]1[C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:8]([C:4]2[C:3]([F:29])=[C:2]([NH:1][CH2:30][C:32]4[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:33]=4[C:34]([OH:36])=[O:35])[CH:7]=[CH:6][CH:5]=2)=[CH:9][N:10]=1)=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:15]=3)(=[O:27])[NH2:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 176Acetic Acid2×HCID 5049666Sodium triacetoxyborohydride2×HCID 679950434-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamideHCID 772303602-Formyl-5-methylbenzoic acid

Product 1

HCID 679947772-((3-(1-Carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylamino)methyl)-5-methylbenzoic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a light orange, homogeneous solution of 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (0.0767 g, 0.194 mmol), 2-formyl-5-methylbenzoic acid (0.096 g, 0.583 mmol) and acetic acid (0.033 mL, 0.583 mmol) in dichloromethane (3.89 mL) and THF (2.59 mL) under nitrogen was added sodium triacetoxyborohydride (0.206 g, 0.972 mmol). The reaction was stirred overnight. More sodium triacetoxyborohydride (0.206 g, 0.972 mmol) and acetic acid (0.033 mL, 0.583 mmol) were added. After 4.5 hr, water (3 mL) was added, and the reaction was stirred for 10 min. EtOAc (50 mL) and water (20 mL) were added, and the layers were separated. The organic layer was washed with water (6×20 mL) and brine (20 mL), dried over MgSO4, and concentrated in vacuo to give a crude product used in subsequent step.

Workup

  1. waitAfter 4.5 hr
  2. stirringthe reaction was stirred for 10 min
  3. customthe layers were separated
  4. washThe organic layer was washed with water (6×20 mL) and brine (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-feedbc9b6c5d4ca9ab7d0560d2341670
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685969B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes