2-(((Tert-butoxy)carbonyl)amino)-2-(4-chlorophenyl)acetic acid → tert-butyl (1-(4-chlorophenyl)-2-((5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-3-yl)amino)-2-oxoethyl)carbamate

HRID 82324Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][C:21]1[CH:22]=[C:23]([C:27]([C:29]2[C:37]3[CH:36]=[N:35][CH:34]=[N:33][C:32]=3[N:31]([CH:38]([CH3:40])[CH3:39])[CH:30]=2)=[O:28])[CH:24]=[N:25][CH:26]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1>N1C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([NH:20][C:21]2[CH:26]=[N:25][CH:24]=[C:23]([C:27]([C:29]3[C:37]4[CH:36]=[N:35][CH:34]=[N:33][C:32]=4[N:31]([CH:38]([CH3:40])[CH3:39])[CH:30]=3)=[O:28])[CH:22]=2)=[O:12])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To pyridine (4 mL) in a sealed vessel was added 2-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid (67 mg, 0.24 mmol) (see Preparation 303), (5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (52 mg, 0.18 mmol) (see Preparation 95) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (105 mg, 0.28 mmol). The reaction was heated at 50° C. for 18 hours and then evaporated in vacuo and purified by column chromatography (gradient of 100:0 to 88:12 DCM:MeOH) to give the title compound in 49% yield, 64 mg. LCMS (basic): Rt=0.81 min; m/z 549 [M+H]+.

Workup

customevaporated in vacuo
custompurified by column chromatography (gradient of 100:0 to 88:12 DCM:MeOH)

Sources & evidence

ORD record: ord-854391341cbd40758f3eb0753cebe170
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Reaction notes

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