Water → HCID 71255363, compound

HRID 540300Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2([N:18]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][O:16][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:33])[CH:8]=2)[N:3]=1.[F:34][C:35]1([F:46])[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[CH2:39][NH:38][CH2:37][CH2:36]1.C(N(CC)CC)C.O>CN(C)C=O>[CH2:19]([N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1([CH2:13][NH:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:33])[CH:8]=3)[N:3]=[C:2]([N:38]3[CH2:37][CH2:36][C:35]([F:34])([F:46])[C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=4[CH2:39]3)[N:11]=2)[CH2:17][O:16][CH2:15]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-chloro-N-{[3-(dibenzylamino)oxetan-3-yl]methyl}-6-methylquinazolin-4-amine (200 mg, 0.436 mmol) in N,N-dimethylformamide (3 mL) was added 5,5-difluoro-1,3,4,5-tetrahydro-2H-2-benzazepine (80 mg, 0.436 mmol) and triethylamine (89 mg, 0.872 mmol). The mixture was heated at 120° C. for 30 minutes under microwave irradiation. The reaction was poured into water (10 mL) and extracted with dichloromethane (15 mL×3). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 20% ethyl acetate in petroleum ether) to afford 190 mg of the product as a brown solid (yield was 72%).

Workup

extractionextracted with dichloromethane (15 mL×3)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (eluting with 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-db609317a0c9433eae7280ac0df5f145
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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