HCID 59380419, compound → HCID 67358116, compound

HRID 2353840Notes

Reaction equation

HRID 2353840 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29]([O:31][CH2:32][CH:33]([OH:46])[CH2:34][N:35]5C(=O)C6C(=CC=CC=6)C5=O)=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1>CCO>[NH2:35][CH2:34][CH:33]([OH:46])[CH2:32][O:31][C:29]1[CH:28]=[CH:27][C:26]2[C:19]3[C:18]([NH:17][C:4]4[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=5)=[C:2]([Cl:1])[CH:3]=4)=[N:23][CH:22]=[N:21][C:20]=3[S:24][C:25]=2[CH:30]=1

Participants

3

Reactant 1

HCID 59380419HCID 59380419, compound

Product 1

HCID 67358116HCID 67358116, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude material 2-(3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-benzo[4,5]thieno[2,3-d]pyrimidin-7-yloxy}-2-hydroxy-propyl)-isoindole-1,3-dione (216 mg, 0.33 mmol, from Step 1) in EtOH (5 mL) was added hydrizine (1 mL) under nitrogen. The reaction was stirred at rt for 15 h. The solvent was removed in vacuo. The crude material was purified by preparative HPLC to give 1-amino-3-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]oxy}propan-2-ol as a white solid (21 mg, 12%). 1H-NMR (CD3OD) δ 8.23 (s, 1H), 8.07 (d, J=9.2 Hz, 1H), 7.59 (d, J=2.7 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.31 (dd, J=2.7, 9.0 Hz, 1H), 7.26 (m, 1H), 7.16 (d, J=7.8 Hz, 1H), 7.11 (d, J=9.7 Hz, 1H), 7.03 (dd, J=2.3, 9.0 Hz, 1H), 6.96 (d, J=9.2 Hz, 1H), 6.92 (td, 1H), 5.04 (s, 2H), 3.94 (m, 3H), 2.81 (m, 2H), LCMS RT=2.84 min, [M+H]+=525.1.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-6625aa830c92486bb2debb42c9c44c9b
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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