2-(2-Pyrrolidinyl)-1,3-thiazole → HCID 16038010, compound

HRID 1806229Notes

Reaction equation

HRID 1806229 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[NH:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[C:37]1[S:38][CH:39]=[CH:40][N:41]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:32]5[CH2:36][CH2:35][CH2:34][CH:33]5[C:37]5[S:38][CH:39]=[CH:40][N:41]=5)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 33580902-(2-Pyrrolidinyl)-1,3-thiazoleHCID 5049666Sodium triacetoxyborohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 16038010HCID 16038010, compoundYield 30.9%

Procedure

Following the general procedure of example 1, 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2-(2-pyrrolidinyl)-1,3-thiazole (132.4 mg, 0.86 mmol) and NaBH(OAc)3 (58.0 mg, 0.303 mmol) were reacted to give the title compound (20.0 mg, 30.4%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c8f2f1a9e77b457ea6b981ddbbc06453
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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