Diisopropylethylamine → HCID 57377955, compound

HRID 1802214Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7](=[O:24])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([OH:27])=O)[CH:4]=[N:3]1.Cl.FC1CNC1.C([N:36]([CH:40]([CH3:42])C)[CH:37]([CH3:39])C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]([NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[N:17]=[C:11]3[CH:10]=2)=[O:24])=[C:5]([C:25]([N:36]2[CH2:37][CH2:39][CH2:42][CH2:40]2)=[O:27])[CH:4]=[N:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (150 mg, 0.404 mmole), 3-fluoroazetidine hydrochloride (202 ul, 2.42 mmole), N-ethyldiisopropylamine (282 ul, 1.62 mmole) and 1-propanephosphonic acid cyclic anhydride (50% in ethyl acetate, 606 ul, 1.01 mmole) in tetrahydrofurane (7 ml) is stirred for 22 h at 70° C. The solvent is removed under reduced pressure and the residue (772 mg) is triturated for 1 hr with sat. aqueous sodium bicarbonate solution (30 ml). The solid is collected by filtration, washed with water and dried affording 1-methyl-N-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-4-(pyrrolidine-1-carbonyl)-1H-pyrazole-5-carboxamide (152 mg, 88.7%) as a white solid. mp.: 210-2° C. MS: m/z=429.4 (M+H+)

Workup

customThe solvent is removed under reduced pressure
customthe residue (772 mg) is triturated for 1 hr with sat. aqueous sodium bicarbonate solution (30 ml)
filtrationThe solid is collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-555a5c8f8f814f93ae26fb51b4913fc6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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