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Acetic Anhydride → HCID 11611808, compound

HRID 646922
Notes
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Reaction equation

HRID 646922 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[CH3:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][C:16]=2[NH:27][C:28]([C:30]2[NH:31][CH:32]=[C:33]([C:35]#[N:36])[CH:34]=2)=[O:29])[CH2:11][CH2:10]1.C(OC(=O)C)(=O)C.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[C:3]([N:24]1[CH2:23][CH2:22][N:21]([C:19]2[CH:18]=[CH:17][C:16]([NH:27][C:28]([C:30]3[NH:31][CH:32]=[C:33]([C:35]#[N:36])[CH:34]=3)=[O:29])=[C:15]([N:12]3[CH2:13][CH2:14][CH:9]([CH3:8])[CH2:10][CH2:11]3)[CH:20]=2)[CH2:26][CH2:25]1)(=[O:4])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86604896HCID 86604896, compound

Product 1

HCID 11611808HCID 11611808, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To 4-cyano-1H-pyrrole-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-4-piperazin-1-yl-phenyl]-amide trifluoroacetic acid salt (as prepared in Example 56, step (b)) (30 mg, 0.048 mmol) in dichloromethane (5 mL) was added acetic anhydride (7.0 μL, 0.072 mmol) and DIEA (31 μL, 0.18 mmol) and the mixture was stirred for 5 h at RT. The mixture was poured into saturated aq sodium bicarbonate (5 mL), extracted with dichloromethane (5 mL), and the organic layer was dried (Na2SO4). The solvents were removed in vacuo and the resulting residue was purified by silica gel preparative TLC eluting with 10% methanol in dichloromethane to yield 4.9 mg (23%) of the title compound as an off-white solid. 1H-NMR (400 MHz, CDCl3): δ 10.57 (br s, 1H), 8.99 (s, 1H), 8.27 (d, 1H, J=8.8 Hz), 7.45 (dd, 1H, J=3.1, 1.3 Hz), 6.851 (s, 1H), 6.81 (d, 1H, J=3.5 Hz), 6.73 (dd, 1H, J=8.9, 2.6 Hz), 3.79 (m, 2H), 3.64 (m, 2H), 3.17-2.96 (m, 4H), 2.74 (m, 2H), 2.70 (m, 2H), 2.15 (s, 3H), 1.87-1.84 (m, 2H), 1.58 (m, 1H), 1.44-1.34 (m, 2H), 1.08 (d, 3H, J=6.5 Hz). LC-MS (ESI, m/z): Calcd. for C24H31N6O2, 435.2 (M+H); found: 435.1.

Workup

  1. extractionextracted with dichloromethane (5 mL)
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. customThe solvents were removed in vacuo
  4. customthe resulting residue was purified by silica gel preparative TLC
  5. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-eb4b81a0bd66440f80891da76c064a40
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07705042B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes