Ethyl chloroformate → HCID 25221334, compound

HRID 1642488Notes

Reaction equation

[CH3:1][C:2]1([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C@@H:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C@H:16]4[NH:15][C:14]3=[O:22])[CH2:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3]1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[O:22]=[C:14]1[N:13]([CH:10]2[CH2:11][CH2:12][N:7]([C:2]3([CH3:1])[CH2:6][CH2:5][N:4]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:3]3)[CH2:8][CH2:9]2)[C@@H:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C@H:16]2[NH:15]1

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 57619791HCID 57619791, compound

Product 1

HCID 25221334HCID 25221334, compound

Procedure

Following the procedure used in step G of the example 8 and starting with (3aR,7aR)-1-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one (160 mg, 0.522 mmol) and ethyl chloroformate (85 mg, 0.783 mmol), the title compound was obtained as a gum (120 mg). 1H NMR (Methanol-D4) δ 4.60 (brs, 1H), 4.13-4.08 (q, 2H), 3.74-3.51 (m, 4H), 3.43-3.34 (m, 2H), 3.20 (br d, 1H), 3.04-2.90 (m, 3H), 2.73 (br s, 1H), 2.4-2.31 (m, 3H), 1.98-1.60 (br m, 8H), 1.43 (m, 3H), 1.25 (t, 3H), 1.10 (s, 3H). MS (M+1): 379.34.

Sources & evidence

ORD record: ord-5ee06c6d12e240d7b7ea5e1877d1fd0f
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119661B2

Reaction notes

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