4-Chlorobenzenesulfonyl chloride → Trifluoroacetate

HRID 1043862Notes

Reaction equation

HRID 1043862 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.[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1.C(#N)C.O.[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55]>CN(C)C=O>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([N:25]2[CH2:26][CH2:27][CH:22]([CH2:21][NH:20][C:16]3[N:15]=[C:14]([C:2]4[C:12]5=[C:13]6[C:8](=[CH:9][CH:10]=[CH:11]5)[CH2:7][CH2:6][CH2:5][N:4]6[CH:3]=4)[CH:19]=[CH:18][N:17]=3)[CH2:23][CH2:24]2)(=[O:46])=[O:45])=[CH:40][CH:39]=1.[F:52][C:53]([F:58])([F:57])[C:54]([O-:56])=[O:55]

Participants

7

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22145617Water TFA acetonitrileHCID 67250798HCID 67250798, compound

Product 2

HCID 84468TrifluoroacetateHCID 58329516HCID 58329516, 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 4-chlorobenzene-1-sulfonyl chloride (23 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 N-((1-(4-chlorophenylsulfonyl)piperidin-4-yl)methyl)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-amine as a trifluoroacetate salt. M.p.=140-142° C.; 1H NMR 400 MHz (DMSO-d6) δ 8.53 (s, 1H), 8.27 (s, 1H), 8.13 (s, 1H), 8.08 (d, J=6.7 Hz, 2H), 7.73 (d, J=9.0 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H), 7.17 (m, 2H), 7.04 (d, J=7.0 Hz, 1H), 4.29 (m, 2H), 3.68 (d, J=12.1 Hz, 2H), 3.41 (s, 2H), 2.97 (t, J=5.9 Hz, 2H), 2.33 (t, J=11.7 Hz, 2H), 2.18 (m, 2H), 1.95 (d, J=12.9 Hz, 2H), 1.75 (m, 1H), 1.31 (m, 2H); LCMS: 522 [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-04d7ffe40bfc4f55b9d6d39b8c716aca
Source dataset
uspto-grants-2013_10
Patent number
US08563567B2

Reaction notes

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