Ethanol → HCID 59380419, compound

HRID 2353839Notes

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]([OH:31])=[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.O1CC1C[C:35]1[CH:45]=[CH:44][CH:43]=[C:37]2[C:38]([NH:40][C:41](=[O:42])[C:36]=12)=[O:39].[CH2:47](N(CC)CC)C.[CH3:54][CH2:55][OH:56]>>[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][CH2:54][CH:55]([OH:56])[CH2:47][N:40]5[C:41](=[O:42])[C:36]6[C:37](=[CH:43][CH:44]=[CH:45][CH:35]=6)[C:38]5=[O:39])=[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

Participants

Reactant 4

HCID 702Ethanol

HCID 8471Triethylamine

HCID 21894791HCID 21894791, compound

HCID 59380394HCID 59380394, compound

Product 1

HCID 59380419HCID 59380419, compound

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-ol (150 mg, 0.33 mmol) in EtOH (15 mL) was added (2,3-epoxypropyl)phthalimide (101.2 mg, 0.50 mmol, 1.5 equiv) and triethylamine (1.68 mg, 0.02 mmol, 0.05 equiv) under nitrogen. The reaction mixture was stirred at 80° C. for 15 h and then cooled to rt. The resulting mixture was concentrated in vacuo. The crude material (216 mg, 0.33 mmol) was directly used in the next step without further purification, LCMS RT=3.89 min, [M+H]+=655.1.

Workup

temperaturecooled to rt
concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-6d136a12233d4a66a65ee83ece02758d
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750017B2

Reaction notes

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