Pivaloyl chloride → Trifluoroacetate

HRID 1043863Notes

Reaction equation

HRID 1043863 reaction equation
Cl.[C:2]1([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=2)[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH2:7][CH2:6][CH2:5][N:4]3[CH:3]=1.C(N(CC)C(C)C)(C)C.[C:37](Cl)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39].C(#N)C.O.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>CN(C)C=O>[C:2]1([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:24][CH2:23]3)[N:15]=2)[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH2:7][CH2:6][CH2:5][N:4]3[CH:3]=1.[F:48][C:49]([F:54])([F:53])[C:50]([O-:52])=[O:51]

Participants

7

Reactant 4

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 22145617Water TFA acetonitrileHCID 67250798HCID 67250798, compound

Product 2

HCID 84468TrifluoroacetateHCID 67250344HCID 67250344, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-N-(piperidin-4-ylmethyl)pyrimidin-2-amine hydrochloride (77 mg, 0.2 mmol), N,N-diisopropylethylamine (174 μL, 1.0 mmol) in N,N-dimethylformamide (2 mL) was treated with pivaloyl chloride (24 mg, 0.2 mmol) and stirred at room temperature. Upon reaction completion the product was isolated by High Performance Liquid Chromatography using acetonitrile/water/trifluoroacetic acid as eluent. The pure product containing fractions were concentrated under reduced pressure to afford 1-(4-((4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-ylamino)methyl)piperidin-1-yl)-2,2-dimethylpropan-1-one as a trifluoroacetate salt. M.p.=170-172° C.; 1H NMR 400 MHz (DMSO-d6) δ 8.47 (s, 1H), 8.19 (m, 1H), 8.09 (d, J=6.3 Hz, 1H), 7.98 (m, 1H), 7.15 (m, 2H), 7.03 (d, J=7.0 Hz, 1H), 4.28 (m, 4H), 2.98 (t, J=5.9 Hz, 2H), 2.78 (t, J=12.1 Hz, 2H), 2.18 (m, 2H), 1.99 (m, 1H), 1.81 (d, J=11.7 Hz, 2H), 1.19 (s, 9H), 1.14 (m, 2H); LCMS: 432 [M+H].

Workup

  1. customUpon reaction completion the product
  2. customwas isolated by High Performance Liquid Chromatography
  3. additionThe pure product containing fractions
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-8629c17a23584f85815feaa0d608af3b
Source dataset
uspto-grants-2013_10
Patent number
US08563567B2

Reaction notes

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