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Trimethylsilyl isocyanate → 3-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-azetidine-1-carboxamide

HRID 2046933
Notes
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Reaction equation

HRID 2046933 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:18]([CH:19]([C:21]5[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=5[Cl:29])[CH3:20])=[CH:17][NH:16][C:13]4=[N:14][CH:15]=3)[CH:7]=[N:6]2)[CH2:2]1.C[Si]([N:34]=[C:35]=[O:36])(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:29][C:22]1[C:23]([F:28])=[CH:24][CH:25]=[C:26]([Cl:27])[C:21]=1[CH:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([C:8]3[CH:7]=[N:6][N:5]([CH:3]4[CH2:2][N:1]([C:35]([NH2:34])=[O:36])[CH2:4]4)[CH:9]=3)[CH:11]=2)[NH:16][CH:17]=1)[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 462154755-(1-azetidin-3-yl-1H-pyrazol-4-yl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 673647523-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-azetidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A mixture of 5-(1-azetidin-3-yl-1H-pyrazol-4-yl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine (6.0 mg, 0.014 mmol), trimethylsilyl isocyanate (5.0 μL, 0.037 mmol), DIPEA (0.02 mL, 0.09 mmol) and DCM (2 mL) was stirred at rt for 30 min. The solution was concentrated in vacuo, redissolved in MeOH and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.89 (d, J=7.1 Hz, 3 H), 4.29-4.36 (m, 2 H), 4.42 (t, J=8.5 Hz, 2 H), 5.20-5.34 (m, 2 H), 7.14-7.23 (m, 1 H), 7.37 (d, J=1.3 Hz, 1 H), 7.39-7.52 (m, 2 H), 7.69 (s, 1 H), 7.94 (s, 1 H), 8.33 (s, 1 H). MS (ES+): m/z 473.11 (100) [MH+]. HPLC: tR=2.86 min (ZQ3, polar—5 min).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH
  3. custompurified via HPLC
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-a802125ae74e46dbb0215722e21e3970
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592448B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes