Diisopropylethylamine → 2-Methyl 6(thieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxylic acid (2-morpholin-4-yl)ethylamide
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]=[CH:19][S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:21]([OH:23])=O.[NH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[N:27]1([CH2:26][CH2:25][NH:24][C:21]([C:3]2[C:4]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:17]=[CH:16][N:15]=[C:14]5[CH:18]=[CH:19][S:20][C:13]=45)=[CH:7][C:5]=3[S:6][C:2]=2[CH3:1])=[O:23])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1Participants
5
Reactant 4
Product 1
Procedure
This material was prepared from the reaction of 2-methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxylic acid 133a (93 mg, 0.27 mmole) with 4-(2-aminoethyl)morpholine (0.12 mL, 0.82 mmole), diisopropylethylamine (0.10 mL, 0.55 mmole), and HBTU (155 mg, 0.41 mmole) in a manner similar to that previously described for example 117 to give a white crystalline solid (35 mg, 28%). 1H NMR (DMSO-d6, 300 MHz) δ8.51 (1H, d, J=5.27 Hz), 8.28 (1H, t, J=5.37 Hz), 8.15 (1H, d, J=5.46 Hz), 7.94 (1H, dd, J=2.26 Hz), 7.94 (1H, d, J=8.48 Hz), 7.59 (1H, d, J=5.46 Hz), 7.33 (1H, dd, J=2.26, 8.85 Hz), 6.64 (1H, d, J=5.27 Hz), 3.58 (4H, t, J=4.33 Hz), 3.43 (2H, q, J=6.09 Hz), 3.32 (2H, m), 2.63 (3H, s), 2.52-2.39 (4H, m).
Sources & evidence
- ORD record
- ord-b391b8bb69484cee96124338e5783c84
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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