Ethanamine, 2-fluoro-, hydrochloride → HCID 57937325, compound

HRID 1435537Notes

Reaction equation

HRID 1435537 reaction equation
Cl.[F:2][CH2:3][CH2:4][NH2:5].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:39]([C:43]1[N:47]([CH2:48][CH:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[C:46]2[CH:55]=[CH:56][C:57]([S:59]([N:62]3[CH:66]=[CH:65][C:64]([C:67](O)=[O:68])=[CH:63]3)(=[O:61])=[O:60])=[CH:58][C:45]=2[N:44]=1)([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C>[C:39]([C:43]1[N:47]([CH2:48][CH:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[C:46]2[CH:55]=[CH:56][C:57]([S:59]([N:62]3[CH:66]=[CH:65][C:64]([C:67]([NH:5][CH2:4][CH2:3][F:2])=[O:68])=[CH:63]3)(=[O:61])=[O:60])=[CH:58][C:45]=2[N:44]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579373191-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid

Product 1

HCID 57937325HCID 57937325, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 31, method B, using 2-fluoroethylamine hydrochloride (0.70 g, 6.98 mmol), N,N-diisopropylethylamine (2.13 ml, 12.3 mmol), HATU (1.46 g, 3.83 mmol) and 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (3.49 mmol) in DMF (90 mL). The crude product was purified by MPLC on silica gel using EtOAc to provide the title compound as white solid. Yield: 0.74 g (35%). 1H NMR (400 MHz, METHANOL-D4) δ 1.40-1.46 (m, 5 H), 1.51 (dd, J=13.28, 3.71 Hz, 2 H), 1.57 (s, 9 H), 3.52 (td, J=26.02, 5.15 Hz, 2 H), 3.86 (dd, J=11.52, 3.52 Hz, 2 H), 4.39 (d, J=7.81 Hz, 2 H), 4.43 (m, 2 H), 6.64 (dd, J=3.32, 1.56 Hz, 1 H), 7.26-7.28 (m, 1 H), 7.80-7.83 (m, 1 H), 7.87-7.93 (m, 2 H), 8.24 (d, J=1.17 Hz, 1 H); MS (APPI) (M+H)+=491.3.

Workup

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

Sources & evidence

ORD record
ord-b681a9cf01724d8996712817c3dddc72
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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