Trifluoroacetic acid → HCID 57640328, compound

HRID 2111919Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15](CC2CC2)[C:16]2[S:20][C:19]([CH3:21])=[N:18][C:17]=2[CH3:22])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:27]1(OC)[CH:32]=[CH:31][CH:30]=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH:32]1([CH2:27][N:14]([CH2:15][C:16]2[S:20][C:19]([CH3:21])=[N:18][C:17]=2[CH3:22])[CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:30][CH2:31]1

Participants

Conditions

Temperature: 0 °C

Procedure

4-{[Cyclopropylmethyl-(2,4-dimethyl-thiazol-5-ylmethyl)]-amino}-piperidine-1-carboxylic acid tert-butyl ester (1.96 g, 5.18 mmol) is added to a stirred solution of dichloromethane (5 ml) and anisole (9.0 ml, 82.8 mmol). The reaction is cooled to 0° C. Trifluoroacetic acid (6.0 ml, 72.9 mmol) is then added. The reaction is stirred for 20 minutes at 0° C. and then for 5 h at room temperature. The reaction is loaded onto a pre-washed SCX-2 (10 g) column and washed with methanol (200 ml). The product is then eluted off with 2M ammonia in methanol (100 ml) and concentrated on a rotary evaporator to yield (1.25 g, 87%) of N-(cyclopropylmethyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]piperidin-4-amine: mass spectrum (ion spray): m/z=280.2 (M+1); 1H NMR (CDCl3): δ=3.75 (2H, s), 3.19-3.11 (2H, m), 2.81-2.73 (1H, m), 2.65-2.52 (5H, m), 2.42 (2H, d), 2.32 (3H, s), 1.76 (3H, brd), 1.50-1.38 (2H, m), 0.89-0.80 (1H, m), 0.52-0.44 (2H, m), 0.11-0.05 (2H, m).

Workup

waitfor 5 h at room temperature
washwashed with methanol (200 ml)
washThe product is then eluted off with 2M ammonia in methanol (100 ml)
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-c661e171784c4ed685bfe974cdfebc62
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521462B2

Reaction notes

Loading…