4-Amino-1-Boc-piperidine → HCID 85904484, compound

HRID 897236Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[O:5][C:4](=[O:16])[CH:3]=1.[NH2:17][CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1.ClC1C2C(=CC(Cl)=C(Cl)C=2)OC(=O)C=1.O1C2C=CC(N3CCC(N)CC3)=CC=2OC1>>[NH:21]1[CH2:22][CH2:23][CH:18]([NH:17][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=3)[O:5][C:4](=[O:16])[CH:3]=2)[CH2:19][CH2:20]1

Participants

Reactant 4

HCID 12682914-Amino-1-Boc-piperidine

HCID 22348121HCID 22348121, compound

HCID 22348184HCID 22348184, compound

HCID 28492219HCID 28492219, compound

Product 1

HCID 85904484HCID 85904484, compound

Procedure

4-(Piperdin-4-ylamino)-6-trifluoromethyl-chromen-2-one was prepared according to the procedure described in Example 76, except that crude 4-chloro-6-trifluoromethyl-chromen-2-one (423 mg, 1.7 mmol) and 4-amino-1-N-Boc-piperidine (359 mg, 1.79 mmol) were used in place of 4,6,7-trichlorochromen-2-one and 1-benzo[1,3]dioxol-5-yl-piperdin-4-ylamine, to give a white solid (521 mg). Removal of the BOC protecting group provided the free base as a white solid (272 mg, 69%). MS (APCI) m/z 313 [M+H]+, 311 [M−H]+; 1H NMR (300 MHz, DMSO-D6) δ ppm 1.81 (m, 2H) 2.10 (m, 2H) 3.03 (m, J=2.37 Hz, 2H) 3.39 (m, 2H) 3.84 (m, 1H) 5.50 (s, 1H) 7.52 (d, J=8.48 Hz, 1H) 7.68 (d, J=7.80 Hz, 1H) 7.95 (d, J=8.82 Hz, 1H) 8.66 (s, 1H) 8.72 (s, 2H).

Sources & evidence

ORD record: ord-dab0abc54e04473f9c831fc1db1b180a
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921821B2

Reaction notes

Loading…