1,2-Dichloroethane → HCID 10231196, compound

HRID 2216321Notes

Reaction equation

[C:1]([NH:20][CH2:21][C:22](O)=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([NH:36][C:37]([C@@H:39]3[CH2:43][CH2:42][CH2:41][NH:40]3)=[O:38])[CH:34]=2)[N:29]=[CH:28][N:27]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C)C=O>[NH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([NH:36][C:37]([C@@H:39]3[CH2:43][CH2:42][CH2:41][N:40]3[C:22](=[O:23])[CH2:21][NH:20][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:38])[CH:34]=2)[N:29]=[CH:28][N:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-Tritylglycine (1.58 g, 5.0 mmol) and (2S)-N-(4-amino-6-quinazolinyl)-2-pyrrolidinecarboxamide (1.15 g, 4.5 mmol) were dissolved in 11 mL N,N-dimethylformamide and cooled to 0° C. HOBt (0.770 g, 5.0 mmol) was added and pH was set to 8 with N-methylmorpholine. After 10 minutes EDC (0.978 g, 5.0 mmol) was added and the mixture was stirred for 12 hours. The solvent was evaporated and the crude product was purified with column chromatography using chloroform/methanol (9/1) as eluant.

Workup

customThe solvent was evaporated
customthe crude product was purified with column chromatography

Sources & evidence

ORD record: ord-c50c05ad104a470da20419f5f74bc29e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112590B2

Reaction notes

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