Prolinol → HCID 11574481, compound

HRID 2075853Notes

Reaction equation

HRID 2075853 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH2:14])=[O:13])=[C:6]2[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O.[OH:22][CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][NH:25]1>CO.C(Cl)Cl>[OH:22][CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH2:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH2:14])=[O:13])=[C:6]2[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 90908ProlinolHCID 76850762HCID 76850762, compound

Product 1

HCID 11574481HCID 11574481, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Treat 5-formyl-3-phenylsulfanyl-1H-indole-2-carboxylic acid amide 13 (m=0, R3=Ph) (50 mg, 0.169 mmol) with 2-hydroxymethylpyrrolidine (46 mg, 0.45 mmol) as described in General Procedure X to afford Iw (42.0 mg, 65.6%) as a tan solid, tlc Rf=0.15 (10% MeOH/CH2Cl2−0.25% Et3N), m/z obs=382 (M+1).

Sources & evidence

ORD record
ord-c0e31d9bb30d4f50942993391bea3ed2
Source dataset
uspto-grants-2011_04
Patent number
US07923466B2

Reaction notes

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