tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate → HCID 58709776, compound

HRID 2375847Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:26]=1>C(O)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:24][C:25]4[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:26]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (110 mg, 0.33 mmol) and 3-amino-1-phenethyl-1H-pyrazole (74 mg, 0.39 mmol) in 1-butanol (3 mL) was heated at 120° C. overnight, LC-MS showed the reaction was complete. The mixture was concentrated, then dissolved in MeOH-DMSO, and purified by MSDP (using water/acetonitrile/HCOOH mixtures) to give the title compound as a brown solid. LC-MS (ES, Pos.): 486 [MH+]. 1H NMR (CD3OD, 400 MHz): δ=1.49 (s, 9H), 2.54 (m, 2H), 3.16 (t, J=7.1 Hz, 2H), 3.65 (m, 2H), 4.12 (m, 2H), 4.32 (t, J=7.1 Hz, 2H), 6.27 (s, 1H), 6.48 (d, J=2.3 Hz, 1H), 6.53 (s, 1H), 7.14-7.28 (m, 5H), 7.36 (d, J=2.3 Hz, 1H), 8.21 (s, 1H).

Workup

concentrationThe mixture was concentrated
dissolutiondissolved in MeOH-DMSO
custompurified by MSDP (using water/acetonitrile/HCOOH mixtures)

Sources & evidence

ORD record: ord-273cd6edd1ac4ad09f4f537f246ca93f
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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