Propylamine → HCID 23660830, compound

HRID 1435480Notes

Reaction equation

HRID 1435480 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:38]([C:42]1[N:46]([CH2:47][CH:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)[C:45]2[CH:54]=[CH:55][C:56]([S:58]([N:61]3[CH:65]=[C:64]([C:66](O)=[O:67])[CH:63]=[N:62]3)(=[O:60])=[O:59])=[CH:57][C:44]=2[N:43]=1)([CH3:41])([CH3:40])[CH3:39]>CN(C=O)C>[C:38]([C:42]1[N:46]([CH2:47][CH:48]2[CH2:49][CH2:50][O:51][CH2:52][CH2:53]2)[C:45]2[CH:54]=[CH:55][C:56]([S:58]([N:61]3[CH:65]=[C:64]([C:66]([NH:4][CH2:1][CH2:2][CH3:3])=[O:67])[CH:63]=[N:62]3)(=[O:60])=[O:59])=[CH:57][C:44]=2[N:43]=1)([CH3:39])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579372951-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid

Product 1

HCID 23660830HCID 23660830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 53, Step A, using n-propylamine (8 mg, 0.13 mmol), HATU (37 mg, 0.09 mmol), DIPEA (0.02 mL, 0.10 mmol) and 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid (40 mg, 0.09 mmol) in DMF (5 mL). The crude product was purified by MPLC on silica gel using EtOAc/DCM (1:1) to provide the title compound as a white solid. The product was converted to its TFA salt. Yield: 32 mg (59%); 1H NMR (400 MHz, CD3OD) δ 0.93 (t, J=7.52 Hz, 3 H), 1.43-1.52 (m, 2 H), 1.52-1.62 (m, 4 H), 1.64 (s, 9 H), 2.25-2.37 (m, 1 H), 3.28-3.36 (m, 4 H), 3.91 (dd, J=11.43, 3.22 Hz, 2 H), 4.48 (d, J=7.62 Hz, 2 H), 7.99-8.11 (m, 3 H), 8.39 (d, J=1.37 Hz, 1 H), 8.77 (s, 1 H); MS (ESI) (M+H)+=487.8; Anal. Calcd for C24H33N5O4S+1.7 TFA+1.8H2O: C, 46.10; H, 5.41; N, 9.81. Found: C, 46.15; H, 5.56; N, 9.48.

Workup

  1. customThe crude product was purified by MPLC on silica gel

Sources & evidence

ORD record
ord-0694ea97da0e451081afb07ac74ef085
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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