Sulfuric Acid → HCID 69621331, compound

HRID 1243884Notes

Reaction equation

C(OC(N1CCC([CH2:14][NH:15][C:16]2[N:21]3[N:22]=[CH:23][C:24]([Br:25])=[C:20]3[N:19]=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])[CH:17]=2)CC1)=O)(C)(C)C.S(=O)(=O)(O)O.O1[CH2:43][CH2:42]OCC1>CO>[Br:25][C:24]1[CH:23]=[N:22][N:21]2[C:16]([N:15]([CH:43]3[CH2:42][CH2:14][NH:15][CH2:16][CH2:17]3)[CH3:14])=[CH:17][C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[N:19][C:20]=12

Participants

Conditions

Temperature: 25 °C

Procedure

4-{[3-Bromo-5-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-ylamino]methyl}piperidine-1-carboxylic acid tert-butyl ester (441 mg, 0.847 mmoles) (prepared as described in Example 460, Step A above) was dissolved in methanol (4.5 mL) and 10% (v/v) conc. sulfuric acid in 1,4-dioxane (11.46 mL) was added. The mixture was stirred at 25° C. for 0.5 h. The product was worked up as described in Preparative Example 241, step B and chromatographed on a silica gel column (15×5 cm) using 8% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give [3-bromo-5-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]piperidin-4-yl methylamine (314.4 mg, 88%): FABMS: m/z 420.0 (MH+); HRFABMS: m/z 420.0585 (MH+). Calcd. for C18H20N5BrCl: m/z 420.0591; δH (CDCl3) 1.34 (2H, m, CH2), 1.86 (2H, m, CH2), 1.91 (1H, m, CH), 2.10 (1H, bm, piperidine-NH), 2.67 (2H, m, CH2), 3.18 (2H, m, CH2), 3.38 (2H, m, CH2), 6.37 (1H, s, H6), 6.53 (1H, m, NH), 7.42 (2H, m, Ar—H), 7.52 (1H, m, Ar—H), 7.76 (1H, m, Ar—H) and 8.06 ppm (1H, s Ar—H); δC (CDCl3) CH2: 31.2, 31.2, 46.2, 46.2, 48.4; CH: 36.4, 89.5, 127.1, 130.1, 130.5, 131.6, 143.8; C: 83.2, 132.1, 138.9, 145.6, 146.4, 158.1.

Workup

customchromatographed on a silica gel column (15×5 cm)

Sources & evidence

ORD record: ord-2a8dfe4c10604719bab16b1e2f701488
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119200B2

Reaction notes

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