Ethanolamine → HCID 23660309, compound

HRID 1435453Notes

Reaction equation

HRID 1435453 reaction equation
CCN(C(C)C)C(C)C.[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:17]2[CH:26]=[CH:27][C:28]([S:30]([N:33]3[CH:37]=[CH:36][C:35]([C:38]([OH:40])=O)=[CH:34]3)(=[O:32])=[O:31])=[CH:29][C:16]=2[N:15]=1)([CH3:13])([CH3:12])[CH3:11].[CH2:41]([CH2:43][NH2:44])[OH:42].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:17]2[CH:26]=[CH:27][C:28]([S:30]([N:33]3[CH:37]=[CH:36][C:35]([C:38]([NH:44][CH2:43][CH2:41][OH:42])=[O:40])=[CH:34]3)(=[O:31])=[O:32])=[CH:29][C:16]=2[N:15]=1)([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 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 23660309HCID 23660309, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 33, step A, using DIPEA (47 uL, 35 mg, 0.27 mmol), 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (60 mg, 0.14 mmol) (see following step B for preparation), ethanolamine (17 mg, 0.27 mmol) and HATU (103 mg, 0.27 mmol) in DMF (5 mL). The crude product was purified by MPLC using EtOAc/MeOH (9:1) on silica gel to give 48 mg (72%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.42-1.58 (m, 4H), 1.61 (s, 9 H), 2.23-2.36 (m, 1 H), 3.25-3.34 (m, 2 H), 3.38 (t, J=5.76 Hz, 2 H), 3.61 (t, J=5.76 Hz, 2 H), 3.86-3.94 (m, 2 H), 4.44 (d, J=7.42 Hz, 2 H), 6.67 (dd, J=3.32, 1.76 Hz, 1H), 7.30 (dd, J=3.32, 2.34 Hz, 1 H), 7.82-7.85 (m, 1 H), 7.94 (d, J=8.8 Hz, 1 H), 7.98 (d, dd, J=8.7, 1.5 Hz, 1 H), 8.28 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=489.3.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-4f7395d6b6e54fec8dab72eb274c238a
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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