Trifluoroacetic acid → HCID 178518849, compound

HRID 855645Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:8]=2)[N:3]=1.C(OC([N:34]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([NH2:43])[CH:41]=2)[C:36](=[O:44])[NH:35]1)=O)(C)(C)C.C([O-])(O)=O.[Na+].C(O)(C(F)(F)F)=O>CN1C(=O)CCC1.C(Cl)Cl>[CH:18]1([C:16]2[CH:17]=[C:13]([NH:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)[CH:8]=4)[N:3]=[C:2]([NH:43][C:40]4[CH:41]=[C:42]5[C:37]([C:36](=[O:44])[NH:35][NH:34]5)=[CH:38][CH:39]=4)[N:11]=3)[NH:14][N:15]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 90 °C

Procedure

To (2-Chloro-6-piperidin-1-yl-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (80 mg, 0.217 mmol) in NMP (1 mL) was added 6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester (65 mg, 0.26 mmol) and heated to 90° C. for 12 hr in a sealed tube. Solution was poured into sat. NaHCO3, resulting in a brown solid. The dried solid was taken up in 5 ml of methylene chloride and treated with 5 mL of TFA for 6 hr. The reaction was evaporated and the title compound was isolated by preparative HPLC to give a yellow solid (47,5 mg). HNMR (500 MHz, dmso); δ11.45 (1H, bs), 10.45 (1H, bs), 8.0 (1H, s), 7.70 (1h, m), 7.6 (1H, m), 7.5 (1H, m), 7.4 (1H, s), 7.1 (1H, m), 6.25 (1H, bs), 3.3 (4H, bs), 2.80–2.55 (7H, m), 0.80 (2H, m), 0.40 (2H, m); HPLC tr=3.51 min (10% to 90% MeCN over 8 min, total time 12 min, 3×150 mm C18 column) FIA m/e 482.5 (M+H), 480.2 (M−H).

Workup

customresulting in a brown solid
customThe reaction was evaporated

Sources & evidence

ORD record: ord-f9261492891f4a6a9732c352d338ad22
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262200B2

Reaction notes

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