Ammonia → HCID 86594674, compound

HRID 1292882Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([C@H:19]5[CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21][C@H:20]5[N:15]4[CH2:14][CH2:13][CH2:12]3)[CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].N>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([C@H:19]5[CH2:24][NH:23][CH2:22][CH2:21][C@H:20]5[N:15]4[CH2:14][CH2:13][CH2:12]3)[CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Reactant 2

HCID 222Ammonia

HCID 86594675HCID 86594675, compound

Product 1

HCID 86594674HCID 86594674, compoundYield 101%

Procedure

The title compound (72.6 mg, 100%) was prepared by the method of Example 112 from tert-butyl (±)-cis-2-(3,4-dichlorophenyl)-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (90 mg, 0.20 mmol) as pale yellow amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.58 (d, 1H, J=2.2 Hz), 7.41 (d, 1H, J=8.4 Hz), 7.32 (dd, 1H, J=2.2, 8.4 Hz), 7.09 (s, 1H), 7.07 (s, 1H), 3.34-3.46 (m, 1H), 3.31 (dt, 1H, J=4.4, 10.7 Hz), 3.03-3.13 (m, 2H), 2.83-2.92 (m, 2H), 2.61-2.78 (m, 4H), 2.10-2.19 (m, 2H), 1.74-1.91 (m, 2H) ppm. MS (CI, NH3): 359 (base, M+H).

Sources & evidence

ORD record: ord-c2c95ac2495a44c592a08c143ed1b770
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238690B2

Reaction notes

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