3-Amino-1-propanol → 6-[(2-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid 3-hydroxypropylamide

HRID 985328Notes

Reaction equation

HRID 985328 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([C:11]1[S:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[O:20][C:21]2[CH:22]=[CH:23][C:24]3[C:28]([C:29]([OH:31])=O)=[C:27]([CH3:32])[S:26][C:25]=3[CH:33]=2)[CH:12]=1)=[O:10].[NH2:34][CH2:35][CH2:36][CH2:37][OH:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>>[OH:38][CH2:37][CH2:36][CH2:35][NH:34][C:29]([C:28]1[C:24]2[CH:23]=[CH:22][C:21]([O:20][C:17]3[CH:16]=[CH:15][N:14]=[C:13]4[CH:12]=[C:11]([C:9]([N:5]5[CH2:6][CH2:7][CH2:8][C@H:4]5[CH2:3][O:2][CH3:1])=[O:10])[S:19][C:18]=34)=[CH:33][C:25]=2[S:26][C:27]=1[CH3:32])=[O:31]

Participants

5

Reactant 4

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 599907896-[(2-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid

Product 1

HCID 599907856-[(2-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid 3-hydroxypropylamideYield 88%

Procedure

This material was prepared by the reaction of 6-[(2-{[(2S)-2-(methoxymethyl)-pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid 121b (45 mg, 0.093 mmole) with 3-amino-1-propanol (21 μL, 0.28 mmole), HBTU (53 mg, 0.14 mmole), and diisopropylethylamine (36 μL, 0.21 mmole) in a manner as previously described for example 117 to give a yellow solid (44 mg, 88%). 1NMR (DMSO-d6, 300 MHz) δ8.58 (1H, d, J=5.27 Hz), 8.36 (1H, t, J=5.46 Hz), 8.03 (1H, s), 7.96 (1H, d, J=2.26 Hz), 7.82 (1H, d, J=8.85 Hz), 7.33 (1H, dd, J=1.70, 8.67 Hz), 6.75 (1H, d, J=5.27 Hz), 4.51 (1H, t, J=5.18 Hz), 4.30 (1H, m), 3.85 (2H, m), 3.37 (2H, m), 3.27 (3H, s), 2.60 (3H, s), 2.09-1.83 (4H, m), 1.71 (2H, m).

Sources & evidence

ORD record
ord-080f6e39850f414191d2aa7ce6bd12a2
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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