1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86607545, compound

HRID 501192Notes

Reaction equation

[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[N:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][N:15]=1.CCN=C=NCCCN(C)C.[NH2:34][O:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][O:37]1>C(Cl)Cl>[O:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH:36]1[O:35][NH:34][C:20]([C:17]1[CH:16]=[N:15][C:14]([N:2]2[CH2:3][CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[N:19][CH:18]=1)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 2-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)pyrimidine-5-carboxylic acid (400 mg) in DCM (10 mL) was added EDCI (390 mg, mmol) at 0° C. After stirring the reaction mixture at 0° C. for 15 min. NH2OTHP (160 mg, mmol) was added. After stirring overnight, the reaction was diluted with DCM (30 mL). The organic layer was washed with saturated sodium bicarbonate and water. The crude product obtained on removal of solvent was purified by column chromatography using EtOAc in hexanes (50%) to obtain N-(tetrahydro-2H-pyran-2-yloxy)-2-[1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidine-5-carboxamide (250 mg, 46.8% yield), m/e=394 (M+1).

Workup

stirringAfter stirring overnight
washThe organic layer was washed with saturated sodium bicarbonate and water
customThe crude product obtained on removal of solvent
customwas purified by column chromatography

Sources & evidence

ORD record: ord-974c202aade74c69ad515f59730bcce2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772245B2

Reaction notes

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