Trifluoroacetic acid methylene chloride → HCID 58466528, compound

HRID 1968893Notes

Reaction equation

HRID 1968893 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:13][N:14]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH3:40])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)=[O:16])[C@H:9]([O:11][CH3:12])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>C(Cl)Cl>[NH2:7][C@@H:8]([C@H:9]([O:11][CH3:12])[CH3:10])[CH2:13][N:14]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][C:35]([CH2:38][CH2:39][CH3:40])=[CH:36][CH:37]=2)=[CH:28][CH:27]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)=[O:16]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86761810HCID 86761810, compound

Product 1

HCID 58466528HCID 58466528, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ((1R,2R)-2-methoxy-1-{[(4′-propyl-biphenyl-4-yl)-(trans-2-pyrazin-2-yl-cyclopropanecarbonyl)-amino]-methyl}-propyl)-carbamic acid tert butyl ester (55 mg) in DCM (1 mL) was treated with TFA/DCM (2/2 mL) for 1 h. The mixture was concentrated to give the titled compound as di-TFA salts (65.5 mg). 1H NMR (400 MHz, MeOD) δ ppm 8.5 (d, J=5.3 Hz, 1H), 8.1-8.2 (m, 2H), 7.5 (t, J=8.0 Hz, 2H), 7.4 (dd, J=8.3, 4.5 Hz, 2H), 7.3 (dd, J=8.2, 3.4 Hz, 2H), 7.2 (dd, J=8.1, 1.5 Hz, 2H), 4.2 (ddd, J=14.8, 8.5, 8.3 Hz, 1H), 3.8 (ddd, J=14.7, 7.9, 4.2 Hz, 1H), 3.4 (qd, J=6.1, 5.9 Hz, 1H), 3.2 (s, 3H), 3.2-3.2 (m, 1H), 2.6 (dddd, J=14.8, 6.1, 5.7, 4.2 Hz, 1H), 2.5 (t, J=7.6 Hz, 2H), 2.0 (q, J=8.3 Hz, 1H), 1.7 (dddd, J=8.9, 7.1, 5.6, 3.7 Hz, 1H), 1.6 (d, J=7.6 Hz, 2H), 1.3-1.4 (m, J=8.5, 5.8, 2.9, 2.9 Hz, 1H), 1.1 (dd, J=6.1, 3.0 Hz, 3H), 0.9 (t, J=7.3 Hz, 3H). LRMS (ESI)=459.3, [(M+H)+, Calcd for C28H35N4O2 459.6].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-e14139e3cb004174878bc915d9a9abee
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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