Dimethylformamide → 4-[4-(Benzothiazol-6-ylamino)-7H-pyrrolo[2,3-d]-pyrimidin-6-yl]-3,6-dihydro-2H-pyridin-1-ylmorpholin-4-ylmethanone

HRID 2375841Notes

Reaction equation

HRID 2375841 reaction equation
Cl.Cl.Cl.[S:4]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.C(N(CC)C(C)C)(C)C.Cl[N:39]1[CH2:44][CH2:43][O:42][CH2:41][C:40]1=C=O.CN(C)[CH:49]=[O:50]>CCOC(C)=O>[S:4]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][N:26]([C:49]([N:39]6[CH2:40][CH2:41][O:42][CH2:43][CH2:44]6)=[O:50])[CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 81531DiisopropylethylamineHCID 69274170Benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochlorideHCID 1317272294-Chloro-carbonylmorpholine

Product 1

HCID 116983224-[4-(Benzothiazol-6-ylamino)-7H-pyrrolo[2,3-d]-pyrimidin-6-yl]-3,6-dihydro-2H-pyridin-1-ylmorpholin-4-ylmethanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine tris-hydrochloride (200 mg, 0.44 mmol) in N,N-dimethylformamide (4 mL) was added N,N-diisopropylethylamine (0.5 mL, 3 mmol). The reaction mixture was stirred at 0° C. for 5 min prior to the addition of 4-chloro-carbonylmorpholine (65 mg, 0.44 mmol) in DMF (0.5 mL). The resulting mixture was stirred at 0° C. for 1 h, diluted with EtOAc (30 mL), washed with water (2×15 mL), brine (15 mL), and dried over anhydrous sodium sulfate. The filtrate was concentrated to 5 mL, and the resulting off-white solid was collected by filtration to give the title compound. LC-MS (ES, Pos.): 462 [MH+], and 1H NMR (DMSO-d6, 400 MHz): δ=2.53 (m, 2H), 3.17 (m, 4H), 3.43 (m, 2H), 3.60 (m, 4H), 3.96 (m, 2H), 6.42 (s, 1H), 6.82 (d, J=1.2 Hz, 1H), 7.88 (dd, J=8.8 Hz, 2.0 Hz, 1H), 8.04 (d, J=8.8 Hz, 1H), 8.34 (s, 1H), 8.91 (d, J=2.0 Hz, 1H), 9.23 (s, 1H), 9.60 (s, 1H), 12.0 (s, 1H).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 h
  2. washwashed with water (2×15 mL), brine (15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe filtrate was concentrated to 5 mL
  5. filtrationthe resulting off-white solid was collected by filtration

Sources & evidence

ORD record
ord-a599a520570c4bf2a7430787be2649e5
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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