Ethyl isocyanatoacetate → Trifluoroacetate

HRID 1043861Notes

Reaction equation

HRID 1043861 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.[N:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:38]=[O:39].C(#N)C.O.[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>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:38]([NH:37][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O: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:50][C:51]([F:56])([F:55])[C:52]([O-:54])=[O:53]

Participants

7

Reactant 4

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 22145617Water TFA acetonitrileHCID 67250798HCID 67250798, compound

Product 2

HCID 84468TrifluoroacetateHCID 67249067HCID 67249067, 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 ethyl 2-isocyanatoacetate (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 ethyl 2-(4-((4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-ylamino)methyl)piperidine-1-carboxamido)acetate as a trifluoroacetate salt. M.p.=170-172° C.; 1H NMR 400 MHz (DMSO-d6) δ 8.51 (s, 1H), 8.25 (m, 1H), 8.18 (m, 1H), 8.10 (d, J=6.3 Hz, 1H), 7.18 (m, 2H), 7.03 (d, J=7.0 Hz, 1H), 6.75 (s, 1H), 4.29 (m, 2H), 4.07 (q, J=7.0 Hz, 2H), 3.96 (d, J=10.3 Hz, 2H), 3.71 (s, 2H), 3.42 (s, 2H), 2.98 (t, J=5.9 Hz, 2H), 2.70 (t, J=11.7 Hz, 2H), 2.18 (m, 2H), 1.92 (m, 1H), 1.76 (d, J=10.2 Hz, 2H), 1.18 (t, J=7.0 Hz, 3H), 1.17 (m, 2H); LCMS: 477 [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-e6d4e50a17ba44cbaa1251026b4dcbfa
Source dataset
uspto-grants-2013_10
Patent number
US08563567B2

Reaction notes

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