Prolinol, (R)- → 5-(5-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

HRID 1806496Notes

Reaction equation

HRID 1806496 reaction equation
[OH:1][CH2:2][C@H:3]1CC[CH2:5][N:4]1[CH2:8][C:9]1[S:13][CH:12]=[C:11]([C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([C:23]([NH2:25])=[O:24])[CH:22]=2)[NH:19][CH:18]=[C:17]3[CH:26]2[CH2:31][CH2:30][N:29]([S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH2:28][CH2:27]2)[CH:10]=1.[NH:38]1CCC[C@@H]1CO>>[NH2:38][C:2](=[O:1])[CH2:3][N:4]([CH2:8][C:9]1[S:13][CH:12]=[C:11]([C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([C:23]([NH2:25])=[O:24])[CH:22]=2)[NH:19][CH:18]=[C:17]3[CH:26]2[CH2:27][CH2:28][N:29]([S:32]([CH:35]([CH3:36])[CH3:37])(=[O:33])=[O:34])[CH2:30][CH2:31]2)[CH:10]=1)[CH3:5]

Participants

3

Reactant 2

HCID 2724541Prolinol, (R)-HCID 577326665-(5-{[(2R)-2-(hydroxymethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

Product 1

HCID 577328445-(5-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamideYield 53.2%

Procedure

The title compound was prepared according to the general procedure of 5-(5-{[(2R)-2-(hydroxymethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide, substituting N2-methylglycinamide (90.13 mg, 1.200 mmol) for (2R)-2-pyrrolidinylmethanol to afford 15 mg of the title compound (53.2%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d89521cf0c9e4d28b680034feec95b22
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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