Pyridine → HCID 22736418, compound

HRID 51476Notes

Reaction equation

HRID 51476 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][C:3]=1[O:24][CH3:25].[N:26]1C=CC=CC=1.Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](Cl)=[O:40]>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:39]([C:34]4[N:33]([CH3:38])[N:26]=[C:36]([CH3:37])[CH:35]=4)=[O:40])=[C:3]([O:24][CH3:25])[CH:4]=3)=[CH:9][N:10]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 135033Picolinoyl Chloride HydrochlorideHCID 227363445-(4-amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 22736418HCID 22736418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80mg, 0.236 mmol) was dissolved in dichloromethane (2.0 mL). Pyridine (2.0 mL) was added followed by 2-pyridinecarbonyl chloride hydrochloride (63 mg, 0.353 mmol). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved in 1 ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N5-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-1,3-dimethyl-1H-5-pyrazolecarboxamide (30 mg, 0.065 mmol). 1H NMR (CDCl3-d) δ 2.11 (m, 4H), 2.32 (s, 3H), 3.66 (m, 2H), 3.99 (s, 3H), 4.13(m, 2H), 4.17 (s, 3H), 4.99 (m, 1H), 5.22 (bs, 2H), 6.46 (s, 1H), 7.03 (s, 1H), 7.07 (s, 1H), 7.12 (d, J=8.2 Hz, 1H), 8.33 (2, 2H), 8.49(d, J=8.2 Hz, 1H). LC/MS: MH+=462.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in 1 ml DMSO
  3. additionmethanol (1 mL) was added
  4. customprecipitate was formed
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-f5aa93bacd9f4874b776131f44196992
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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