Diisopropylethylamine → HCID 70978686, compound

HRID 2281052Notes

Reaction equation

HRID 2281052 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=4)=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.[C:26](O)(=[O:30])[C@H:27]([CH3:29])[OH:28].C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:19]=[CH:20][C:21]([CH2:24][NH:25][C:26](=[O:30])[C@@H:27]([OH:28])[CH3:29])=[CH:22][CH:23]=4)=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 10917558HCID 10917558, compoundHCID 70980750HCID 70980750, compound

Product 1

HCID 70978686HCID 70978686, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{4-[1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]phenyl}methanamine (19 mg, 0.055 mmol), L-lactic acid (9.9 mg, 0.11 mmol, 2 equiv), N,N-diisopropylethylamine (48 μL, 0.27 mmol, 5 equiv) and (1H-benzotriazol-1-yloxy) (tripyrrolidin-1-yl) phosphonium tetrafluoroborate (43 mg, 0.082 mmol, 1.5 equiv) were combined in dichloromethane (1.5 mL) and stirred for 15 minutes. The mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (95:5 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.33 (1H, t, J=6.9 Hz), 8.30 (1H, d, J=8.5 Hz), 7.51 (1H, d, J=8.7 Hz), 7.36-7.32 (4H, m), 4.72 (2H, d, J=7.2 Hz), 4.41-4.33 (2H, m), 4.08-4.03 (1H, m), 1.46-1.38 (1H, m), 1.27 (3H, d, J=6.6 Hz), 0.60-0.55 (2H, m), 0.53-0.50 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 419.1700 [(M+H)+; calculated for C21H22F3N4O2: 419.1689].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by preparative reverse phase HPLC (95:5 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-06147a4e96c5491dbdc07655dc611cda
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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