Acetic Acid → HCID 67994770, compound

HRID 2361322Notes

Reaction equation

HRID 2361322 reaction equation
[NH2:1][C:2]1[C:3]([CH3:34])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][C:16]([NH:21][C:22](=[O:30])[O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:17][CH:18]=4)[NH:13][C:12]=3[C:11]([C:31](=[O:33])[NH2:32])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([CH:45]=O)=[C:40]([CH:44]=1)[C:41]([OH:43])=[O:42].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O1CCCC1.O.CCOC(C)=O>[C:31]([C:11]1[C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:8]([C:4]2[C:3]([CH3:34])=[C:2]([NH:1][CH2:45][C:39]4[CH:38]=[CH:37][C:36]([Cl:35])=[CH:44][C:40]=4[C:41]([OH:43])=[O:42])[CH:7]=[CH:6][CH:5]=2)=[CH:9][N:10]=1)=[CH:18][CH:17]=[C:16]([NH:21][C:22]([O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])=[O:30])[CH:15]=3)(=[O:33])[NH2:32]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 71762095-Chloro-2-formylbenzoic acidHCID 67994568HCID 67994568, compound

Product 1

HCID 67994770HCID 67994770, compound

Reagents, catalysts & solvents 4

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

Procedure

To a homogeneous, light burgundy solution of 2-(trimethylsilyl)ethyl 4-(3-amino-2-methylphenyl)-1-carbamoyl-9H-pyrido[3,4-b]indol-7-ylcarbamate (0.2535 g, 0.533 mmol), 5-chloro-2-formylbenzoic acid (0.246 g, 1.332 mmol), and acetic acid (0.076 mL, 1.332 mmol) in dichloromethane (10.66 mL) and tetrahydrofuran (7.11 mL) under nitrogen was added sodium triacetoxyborohydride (0.339 g, 1.599 mmol). The reaction was stirred overnight. Water (5 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 that was used in the subsequent step.

Workup

  1. stirringthe reaction was stirred 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-fe1016ce7d0c4e678e51eb7557ed1dbf
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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