Trifluoroacetic acid methylene chloride → HCID 86636684, compound

HRID 401442Notes

Reaction equation

HRID 401442 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH3:23])=[C:11]([NH:24][C:25]([C:27]2[C:36](=[O:37])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][CH:28]=2)=[O:26])[CH:10]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=[O:43]>>[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH3:23])=[C:11]([NH2:24])[CH:10]=1.[O:37]=[C:36]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=[C:27]1[C:25]([OH:26])=[O:43]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57567322HCID 57567322, compound

Product 1

HCID 86636684HCID 86636684, compound

Procedure

{2′-Ethoxy-2-[(4-oxo-1,4-dihydroquinoline-3-carbonyl)-amino]-biphenyl-4-ylmethyl}-carbamic acid tert-butyl ester (304) (40 mg, 0.078 mmol) was stirred in a CH2Cl2/TFA mixture (3:1, 20 mL) at room temperature for 1 h. The volatiles were removed on a rotary evaporator. The crude product was purified by preparative HPLC to afford 4-oxo-1,4-dihydroquinoline-3-carboxylic acid (4-aminomethyl-2′-ethoxybiphenyl-2-yl)amine (163) as a tan solid (14 mg. 43%). 1H NMR (300 MHz, DMSO-d6) δ 12.87 (d, J=6.3 Hz, 1H), 11.83 (s, 1H), 8.76 (d, J=6.3 Hz, 1H), 8.40 (s, 1H), 8.26 (br s, 2H), 8.01 (dd, J=8.4 Hz, J=1.5 Hz, 1H), 7.75 (dt, J=8.1 Hz, J=1.2 Hz, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.47-7.37 (m, 2H), 7.24 (s, 2H), 7.15 (dd, J=7.5 Hz, J=1.8 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 7.02 (dt, J=7.5 Hz, J=0.9 Hz, 1H), 4.09 (m, 2H), 4.04 (q, J=6.9 Hz, 2H), 1.09 (t, J=6.9 Hz, 3H); HPLC ret. time 1.71 min, 10-100% CH3CN, 5 min gradient; ESI-MS 414.1 m/z (MH+).

Workup

  1. customThe volatiles were removed on a rotary evaporator
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-80e5d43523404744840660ce61f507f6
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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