Hydrochloric Acid → HCID 89851860, compound

HRID 1746916Notes

Reaction equation

HRID 1746916 reaction equation
[NH2:1][C:2](=[O:37])[C:3](=[O:36])[CH:4]([NH:12][C:13]([C:15]1[C:16]([N:21]2[CH:25]=[C:24]3[CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][C:23]3=[N:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[ClH:38]>ClCCl.O1CCOCC1>[ClH:38].[NH2:1][C:2](=[O:37])[C:3](=[O:36])[CH:4]([NH:12][C:13](=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH:25]=[C:24]2[CH2:26][NH:27][CH2:28][C:23]2=[N:22]1)[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71768809HCID 71768809, compound

Product 1

HCID 89851860HCID 89851860, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2-(3-(4-amino-3,4-dioxo-1-phenylbutan-2-ylcarbamoyl)-pyridin-2-yl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate (50 mg, 0.099 mmol) in dichloromethane (10 mL) 4004 of 4M HCl in dioxan were added and stirred over night at room temperature. The mixture then was concentrated, the remainder treated with MTB and the remaining solid then further purified by chromatography over Chromabond RP-C18 (eluent: water/acetonitrile) to give 30 mg of the titel compound; ESI-MS [M+H]+: 405.1. 1H-NMR (400 MHz, DMSO), δ[ppm]: 10.41 (broad), 8.93 (m, 1H), 8.54 (m, 1H), 8.21 (m, 1H), 8.06 (m, 1H), 7.85 (m, 1H), 7.71 (m, 1H), 7.49 (m, 1H), 7.26 (m, 5H), 5.33 (m, 1H), 4.35-4.16 (m, 5H), 3.12 (m, 1H), 2.84 (m, 1H).

Workup

  1. concentrationThe mixture then was concentrated
  2. additionthe remainder treated with MTB
  3. customthe remaining solid then further purified by chromatography over Chromabond

Sources & evidence

ORD record
ord-c67b8c5ac71e4051bd142746401e5b04
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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