HCID 178445803, compound → HCID 178445769, compound

HRID 713950Notes

Reaction equation

C([C@H]1CC[C@H](OC2C=C3C(=CC=2)N=C(CN2CC(C(O)=O)C2)C=C3C(F)(F)F)CC1)(C)(C)C.C[O:35][C:36]([CH:38]1[CH2:41][N:40]([CH2:42][C:43]2[CH:44]=[C:45]3[C:50](=[CH:51][CH:52]=2)[N:49]=[C:48]([O:53][C@H:54]2[CH2:59][CH2:58][C@H:57]([C:60]([CH3:63])([CH3:62])[CH3:61])[CH2:56][CH2:55]2)[CH:47]=[CH:46]3)[CH2:39]1)=[O:37]>>[C:60]([C@H:57]1[CH2:56][CH2:55][C@H:54]([O:53][C:48]2[CH:47]=[CH:46][C:45]3[C:50](=[CH:51][CH:52]=[C:43]([CH2:42][N:40]4[CH2:41][CH:38]([C:36]([OH:37])=[O:35])[CH2:39]4)[CH:44]=3)[N:49]=2)[CH2:59][CH2:58]1)([CH3:63])([CH3:61])[CH3:62]

Participants

Reactant 2

HCID 178445803HCID 178445803, compound

HCID 178498775HCID 178498775, compound

Product 1

HCID 178445769HCID 178445769, compound

Procedure

Synthesized as per 1-[6-(trans-4-tert-Butyl-cyclohexyloxy)-4-trifluoromethyl-quinolin-2-ylmethyl]-azetidine-3-carboxylic acid using 1-[2-(trans-4-tert-Butyl-cyclohexyloxy)-quinolin-6-ylmethyl]-azetidine-3-carboxylic acid methyl ester as starting material. ESI-MS(M+H+): 397.39; 1H NMR (400 MHz, METHANOL-d4) Shift 8.15 (d, J=8.78 Hz, 1H), 7.89-7.94 (m, 1H), 7.86 (d, J=8.78 Hz, 1H), 7.67 (dd, J=1.88, 8.66 Hz, 1H), 6.96 (d, J=8.78 Hz, 1H), 5.10-5.22 (m, 1H), 4.55 (s, 2H), 4.20-4.47 (m, 4H), 3.71 (quin, J=8.28 Hz, 1H), 2.28 (d, J=9.54 Hz, 2H), 1.92 (d, J=14.31 Hz, 2H), 1.36-1.52 (m, 2H), 1.19-1.36 (m, 2H), 1.06-1.19 (m, 1H), 0.92 (s, 9H).

Sources & evidence

ORD record: ord-f5dc1802f1784820b6240d3357779cf2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186367B2

Reaction notes

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