Acetic Acid → HCID 67994863, compound

HRID 2361316Notes

Reaction equation

HRID 2361316 reaction equation
[NH2:1][C:2]1[C:3]([CH3:37])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][C:16]([N:21]5[CH2:25][CH2:24][CH:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:22]5)=[CH:17][CH:18]=4)[NH:13][C:12]=3[C:11]([C:34]([NH2:36])=[O:35])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([CH:48]=O)=[C:43]([CH:47]=1)[C:44]([OH:46])=[O:45].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O1CCCC1.O.CCOC(C)=O>[Si:27]([O:26][CH:23]1[CH2:24][CH2:25][N:21]([C:16]2[CH:15]=[C:14]3[C:19]([C:20]4[C:8]([C:4]5[C:3]([CH3:37])=[C:2]([NH:1][CH2:48][C:42]6[CH:41]=[CH:40][C:39]([Cl:38])=[CH:47][C:43]=6[C:44]([OH:46])=[O:45])[CH:7]=[CH:6][CH:5]=5)=[CH:9][N:10]=[C:11]([C:34](=[O:35])[NH2:36])[C:12]=4[NH:13]3)=[CH:18][CH:17]=2)[CH2:22]1)([C:30]([CH3:32])([CH3:33])[CH3:31])([CH3:28])[CH3:29]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 71762095-Chloro-2-formylbenzoic acidHCID 86681520HCID 86681520, compound

Product 1

HCID 67994863HCID 67994863, compound

Reagents, catalysts & solvents 4

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

Procedure

To a homogeneous, light orange solution of 4-(3-amino-2-methylphenyl)-7-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-9H-pyrido[3,4-b]indole-1-carboxamide (0.0782 g, 0.152 mmol), 5-chloro-2-formylbenzoic acid (0.070 g, 0.379 mmol), and acetic acid (0.022 mL, 0.379 mmol) in dichloromethane (3.03 mL) and tetrahydrofuran (2.022 mL) under nitrogen was added sodium triacetoxyborohydride (0.096 g, 0.455 mmol), and the mixture was stirred overnight. Water (3 mL) was added, and the reaction was stirred at rt 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 which was used in the subsequent step.

Workup

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

Sources & evidence

ORD record
ord-dd9f8c10135f4efea5436ebce92e3fdb
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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