Methylamine → HCID 23660829, compound

HRID 1435478Notes

Reaction equation

HRID 1435478 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C1COCC1.CCN(C(C)C)C(C)C.[C:41]([C:45]1[N:49]([CH2:50][CH:51]2[CH2:56][CH2:55][O:54][CH2:53][CH2:52]2)[C:48]2[CH:57]=[CH:58][C:59]([S:61]([N:64]3[CH:68]=[C:67]([C:69]([OH:71])=O)[CH:66]=[N:65]3)(=[O:63])=[O:62])=[CH:60][C:47]=2[N:46]=1)([CH3:44])([CH3:43])[CH3:42]>CN(C=O)C>[C:41]([C:45]1[N:49]([CH2:50][CH:51]2[CH2:52][CH2:53][O:54][CH2:55][CH2:56]2)[C:48]2[CH:57]=[CH:58][C:59]([S:61]([N:64]3[CH:68]=[C:67]([C:69]([NH:2][CH3:1])=[O:71])[CH:66]=[N:65]3)(=[O:62])=[O:63])=[CH:60][C:47]=2[N:46]=1)([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 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 23660829HCID 23660829, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 24, Step A, using HATU (37 mg, 0.09 mmol), methylamine in THF (0.07 mL, 2M, 0.14 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) (see following step B for preparation) 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: 15 mg (29%); 1H NMR (400 MHz, CD3OD) δ 1.38-1.46 (m, 2 H), 1.46-1.54 (m, 2 H), 1.54-1.59 (s, 9 H), 2.22-2.36 (m, 1 H), 2.83 (s, 3 H), 3.25-3.35 (m, 2 H), 3.89 (dd, J=11.43, 3.61 Hz, 2 H), 4.36 (d, J=7.42 Hz, 2 H), 7.79 (d, J=8.59 Hz, 1 H), 7.90 (dd, J=8.69, 1.86 Hz, 1 H), 8.01 (s, 1 H), 8.29 (d, J=1.95 Hz, 1 H), 8.72 (s, 1 H); MS (ESI) (M+H)+=459.8; Anal. Calcd for C22H29N5O4S+0.1H2O: C, 57.27; H, 6.38; N, 15.18. Found: C, 57.49; H, 6.55; N, 14.34.

Workup

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

Sources & evidence

ORD record
ord-6797b338c85c482ba60e2c672ac8b320
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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