Acetic Acid → HCID 44600328, compound

HRID 1177603Notes

Reaction equation

HRID 1177603 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)[CH:5]=O.[NH:28]1[CH2:31][CH2:30][CH2:29]1.C(O)(=O)C.ClCCl.CO.C([BH3-])#N.[Na+]>>[N:28]1([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([C:10]3[S:11][C:12]4[C:17]([N:18]=3)=[CH:16][CH:15]=[C:14]([C:19]3([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:21][CH2:20]3)[N:13]=4)=[C:2]([F:1])[CH:3]=2)[CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 6

HCID 176Acetic AcidHCID 887MethanolHCID 6344DichloromethaneHCID 10422AzetidineHCID 5003444Sodium cyanoborohydrideHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 44600328HCID 44600328, compound

Procedure

A solution of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (0.102 g, 0.27 mmol), azetidine (0.037 mL, 0.54 mmol) and acetic acid (0.063 mL, 1.1 mmol) in dichloromethane (3.00 mL, 0.27 mmol) and methanol (2.00 mL, 0.27 mmol), was stirred for 60 min at ambient temperature. The reaction mixture was treated with sodium cyanoborohydride (0.0086 g, 0.14 mmol) and was stirred for 10 min, concentrated in vacuo, and adsorbed onto silica gel. Silica gel chromatography (20-30% EtOAc/hexanes, followed by 40% (3% Et3N/EtOAc)/hexanes gave the title compound. MS (ESI) m/z: Calculated: 415.2; Observed: 416.1 (M++1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c12b1f10613441787832c61382feeac
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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