3-Amino-1-propanol → 2-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid 3-hydroxypropylamide
Reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=5)[S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:27]([OH:29])=O.[NH2:30][CH2:31][CH2:32][CH2:33][OH:34].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[OH:34][CH2:33][CH2:32][CH2:31][NH:30][C:27]([C:3]1[C:4]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=5)[S:20][C:13]=34)=[CH:7][C:5]=2[S:6][C:2]=1[CH3:1])=[O:29]Participants
Reactant 4
Product 1
Procedure
This material was prepared by the reaction of 2-methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid 117b (85 mg, 0.20 mmole) with 3-amino-1-propanol (46 μL, 0.44 mmole), N,N-diisopropylethylamine (77 μL, 0.30 mmole), and HBTU (115 mg, 0.303 mmole) in a manner as previously described for example 117. The crude material was purified by silica gel chromatography (10:30:60% MeOH/CH2Cl2/EtOAc) to give a yellow solid (57 mg, 59%). 1H NMR (DMSO-d6, 300 MHz) δ8.52 (1H, d, J=5.27 Hz), 8.37 (1H, t, J=5.56 Hz), 7.95 (1H, d, J=2.26 Hz), 7.88 (1H, s), 7.82 (1H, d, J=8.85 Hz), 7.40 (1H, s), 7.33 (1H, dd, J=2.35, 8.76 Hz), 7.02 (1H, d, J=0.94 Hz), 6.70 (1H, d, J=5.46 Hz), 4.51 (1H, t, J=5.09 Hz), 3.98 (3H, s), 3.50 (2H, q, J=6.22 Hz), 3.35 (2H, m), 2.60 (3H, s), 1.71 (2H, m).
Workup
- customThe crude material was purified by silica gel chromatography (10:30:60% MeOH/CH2Cl2/EtOAc)
Sources & evidence
- ORD record
- ord-eadebb342a5d40c78f8010c5b297d17d
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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