Ethylamine → HCID 23660108, compound

HRID 1435436Notes

Reaction equation

HRID 1435436 reaction equation
[CH2:1]([NH2:3])[CH3:2].CCN(C(C)C)C(C)C.[C:13]([C:17]1[N:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:20]2[CH:29]=[CH:30][C:31]([S:33]([N:36]3[CH:40]=[C:39]([C:41](O)=[O:42])[CH:38]=[N:37]3)(=[O:35])=[O:34])=[CH:32][C:19]=2[N:18]=1)([CH3:16])([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:13]([C:17]1[N:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:20]2[CH:29]=[CH:30][C:31]([S:33]([N:36]3[CH:40]=[C:39]([C:41]([NH:3][CH2:1][CH3:2])=[O:42])[CH:38]=[N:37]3)(=[O:35])=[O:34])=[CH:32][C:19]=2[N:18]=1)([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 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 23660108HCID 23660108, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 24, Step A, using ethylamine (73 uL, 2.0 M in THF, 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 (48%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.15 (t, J=7.23 Hz, 3 H), 1.40-1.57 (m, 4 H), 1.59 (s, 9H), 2.21-2.41 (m, 1 H), 2.79 (s, 1 H), 3.29-3.35 (m, 4 H), 3.84-3.95 (m, 2 H), 4.41 (d, J=7.42 Hz, 2 H), 7.91 (d, J=9.0 Hz, 1 H), 7.98 (dd, J=9.0, 1.7 Hz, 1 H), 8.03 (s, 1 H), 8.33 (d, J=1.56 Hz, 1 H), 8.74 (s, 1 H); MS (ESI) (M+H)+=474.0; Anal. Calcd for C23H31N5O4S+0.70 TFA+0.30 EtOAc+0.40H2O (590.66): C, 52.67; H, 5.96; N, 11.86. Found: C, 52.63; H, 5.99; N, 11.81.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-12a9ad25eb764498979819c93226757c
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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