Diisopropylethylamine → HCID 59242083, compound

HRID 1876174Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]1[N:20]=[C:19]([N:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH3:22])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:31][CH3:32])[CH:17]=2)[N:12]=1)(C)(C)C.ClC1N=C(N(C2C=CC(OC)=CC=2)C)C2C(=CC=C(OC)C=2)N=1.C(OC(=O)NCCN)(C)(C)C.C(N(C(C)C)CC)(C)C>CCCCO>[NH2:7][CH2:8][CH2:9][NH:10][C:11]1[N:20]=[C:19]([N:21]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[CH3:22])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:31][CH3:32])[CH:17]=2)[N:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

(2-{6-Methoxy-4-[(4-methoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-ethyl)-carbamic acid tert-butyl ester: A mixture of (2-chloro-6-methoxy-quinazoline-4-yl)-(4-methoxy-phenyl)-methyl-amine (0.6 g, 1.81 mmol), (2-amino-ethyl)-carbamic acid tert-butyl ester (0.4 g, 2.54 mmol) and diisopropylethylamine (0.76 mL, 4.4 mmol) in 3 mL of n-BuOH was stirred at 130° C. for 2 days. The solvent was evaporated under reduced pressure. The title compound (0.56 g; 70%) was isolated by preparative TLC (CH2Cl2/MeOH=5/3 as eluent). 1H NMR (DMSO-d6) δ 7.3-7.28 (d, 1H), 7.2 (d, 2H), 7.11-7.08 (d, 1H), 7.02-7.00 (d, 2H), 6.2 (s, 1H), 3.7 (s, 3H), 3.46 (s, 3H), 3.42 (t, 2H), 3.23 (s, 3H), 3.17 (t, 2H), 1.37 (s, 9H); LC-MS (ESI+; 454 ([M+H]+).

Workup

customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-a0b0d9484c4b470280932f28b2fa3772
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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