Cyclobutylamine → HCID 23660107, compound

HRID 1435435Notes

Reaction equation

HRID 1435435 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[C:15]([C:19]1[N:23]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:22]2[CH:31]=[CH:32][C:33]([S:35]([N:38]3[CH:42]=[C:41]([C:43](O)=[O:44])[CH:40]=[N:39]3)(=[O:37])=[O:36])=[CH:34][C:21]=2[N:20]=1)([CH3:18])([CH3:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:15]([C:19]1[N:23]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:22]2[CH:31]=[CH:32][C:33]([S:35]([N:38]3[CH:42]=[C:41]([C:43]([NH:5][CH:1]4[CH2:4][CH2:3][CH2:2]4)=[O:44])[CH:40]=[N:39]3)(=[O:37])=[O:36])=[CH:34][C:21]=2[N:20]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 75645CyclobutylamineHCID 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 23660107HCID 23660107, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 24, Step A, using cyclobutylamine (13 uL, 10 mg, 0.15 mmol), DIPEA (28 uL, 21 mg, 0.16 mmol), 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid (0.073 mmol) and HATU (44 mg, 0.12 mmol) in DMF (2.5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 17 mg (47%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.40-1.56 (m, 4 H), 1.58 (s, 9 H), 1.67-1.79 (m, 2 H), 1.96-2.09 (m, 2 H), 2.22-2.34 (m, 3 H), 3.25-3.34 (m, 2 H), 3.83-3.94 (m, 2 H), 4.34-4.39 (m, 1 H), 4.41 (d, J=7.62 Hz, 2 H), 7.90 (d, J=8.6 Hz, 1 H), 7.97 (dd, J=8.8, 1.8 Hz, 1 H), 8.04 (d, J=0.59 Hz, 1 H), 8.33 (d, J=1.37 Hz, 1 H), 8.77 (d, J=0.59 Hz, 1 H); MS (ESI) (M+H)+=499.8; Anal. Calcd for C25H33N5O4S+0.70 TFA+0.30 EtOAc+0.20H2O (613.09): C, 54.66; H, 6.00; N, 11.42. Found: C, 54.63; H, 5.95; N, 11.51.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-4f54a0b43ab4430692f0c7e37fe5f3cf
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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