Triethylamine → N-(2-tert-butyl-1-(2-hydroxyethyl)-1H-pyrrolo[2,3-c]pyridin-5-yl)-1-(2,2-difiuorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 513093Notes

Reaction equation

HRID 513093 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1([F:41])[O:30][C:29]2[CH:31]=[CH:32][C:33]([C:35]3([C:38]([OH:40])=O)[CH2:37][CH2:36]3)=[CH:34][C:28]=2[O:27]1.[NH2:42][C:43]1[CH:44]=[C:45]2[CH:51]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[N:49]([CH2:56][CH2:57][OH:58])[C:46]2=[CH:47][N:48]=1.C(N(CC)CC)C>CN(C=O)C>[C:52]([C:50]1[N:49]([CH2:56][CH2:57][OH:58])[C:46]2=[CH:47][N:48]=[C:43]([NH:42][C:38]([C:35]3([C:33]4[CH:32]=[CH:31][C:29]5[O:30][C:26]([F:25])([F:41])[O:27][C:28]=5[CH:34]=4)[CH2:36][CH2:37]3)=[O:40])[CH:44]=[C:45]2[CH:51]=1)([CH3:55])([CH3:53])[CH3:54]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 442061031-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarboxylic acidHCID 579081502-(5-amino-2-tert-butyl-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol

Product 1

HCID 25015780N-(2-tert-butyl-1-(2-hydroxyethyl)-1H-pyrrolo[2,3-c]pyridin-5-yl)-1-(2,2-difiuorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (38 mg, 0.10 mmol) was added to a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (24 mg, 0.10 mmol), 2-(5-amino-2-tert-butyl-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol (23 mg, 0.10 mmol) and triethylamine (42 μL, 0.30 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 1 hour. The mixture was filtered and purified by reverse-phase HPLC (10-99% CH3CN—H2O with 0.035% TFA) to yield N-(2-tert-butyl-1-(2-hydroxyethyl)-1H-pyrrolo[2,3-c]pyridin-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide. ESI-MS m/z calc. 457.2. found 458.5 (M+1)+. Retention time 1.77 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.54 (br s, 1H), 8.84 (s, 1H), 7.83 (s, 1H), 7.58 (d, J=1.7 Hz, 1H), 7.45 (d, J=8.3 Hz, 1H), 7.35 (dd, J=8.3, 1.7 Hz, 1H), 6.67 (s, 1H), 4.58 (t, J=5.7 Hz, 2H), 3.76 (t, J=5.7 Hz, 2H), 1.58 (m, 2H), 1.46 (s, 9H), 1.28 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by reverse-phase HPLC (10-99% CH3CN—H2O with 0.035% TFA)

Sources & evidence

ORD record
ord-6893a2cd33064ad5ad94ddc25b19f093
Source dataset
uspto-grants-2015_08
Patent number
US09102672B2

Reaction notes

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