Ammonia methanol → HCID 66604530, compound

HRID 2410906Notes

Reaction equation

[N:1]1([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]4[CH:21]=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:19]=[C:18]([C:28]([O:30]CC)=O)[C:14]=4[NH:15]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH3:33].CO>>[N:1]1([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]4[CH:21]=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:19]=[C:18]([C:28]([NH2:33])=[O:30])[C:14]=4[NH:15]3)=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 66604824HCID 66604824, compound

Product 1

HCID 66604530HCID 66604530, compound

Conditions

Temperature: 135 °C

Procedure

Ethyl 7-(morpholine-4-carbonyl)-3-phenyl-9H-pyrido[3,4-b]indole-1-carboxylate (15 mg, 0.035 mmol) and 7N NH3/MeOH (1.5 mL, 10.50 mmol) were mixed in a sealed microwave tube and heated in microwave at 135° C. for 3.5 hrs. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 401.07 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.83 (s, 1H), 9.07 (s, 1H), 8.43 (m, 4H), 7.89 (s, 1H), 7.84 (s, 1H), 7.53(t, 2H, J=7.6), 7.42 (t, 1H, J=7.3), 7.32 (dd, 1H, J=7.9, 1.5), 3.67-3.43 (bm, 8H).

Workup

concentrationThe mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-001099c0d16743338f1325e65d541afc
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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