Trifluoroacetic acid → HCID 178478423, compound

HRID 2375855Notes

Reaction equation

C(OC([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)(C)(C)C.[NH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][N:29]=[C:28]2[Cl:34].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>FC(F)(F)CO>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[Cl:34][C:28]1[C:27]2[C:31](=[CH:32][CH:33]=[C:25]([NH:24][C:21]3[C:16]4[CH:15]=[C:14]([C:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH:12]=5)[NH:23][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:26]=2)[NH:30][N:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 10 mL sealed tube, to a suspension/solution of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (85.3 mg, 0.229 mmol, 1 eq) and 5-amino-3-chloroindazole (3) (43.3 mg, 0.258 mmol, 1.13 eq) in 2,2,2-trifluoroethanol (TFE) (6 mL), trifluoroacetic acid (TFA) (88 μL, 1.1 mmol, 5 eq) was added and the reaction was allowed to stir for 5 d at 100° C. The reaction was cooled to rt and concentrated under reduced pressure. Purification of the crude material most likely to have been problematic-N-BOC protection carried out for easier purification by chromatography on silica gel. MS (ES+): m/z 365.98/367.98 (30/10) [MH+]. HPLC: tR=0.48 & 1.57 min (ZQ2000, polar—5 min).

Workup

customInto a 10 mL sealed tube
temperatureThe reaction was cooled to rt
concentrationconcentrated under reduced pressure
customPurification of the crude material most likely
customcarried out for easier purification by chromatography on silica gel
customtR=0.48 & 1.57 min (ZQ2000, polar—5 min)

Sources & evidence

ORD record: ord-1da79997e18d45e29d621c5af6cd574b
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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