HCID 17998717, compound → HCID 86700246, compound

HRID 879438Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:37]([CH3:38])=[CH:36][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:28][CH2:27][N:26]5[C:29](C(F)(F)F)=[N:30][N:31]=[C:25]5[CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl.N1N=CN2CCNCC=12>>[C:1]([O:5][C@@H:6]([C:10]1[C:37]([CH3:38])=[CH:36][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:28][CH2:27][N:26]5[CH:29]=[N:30][N:31]=[C:25]5[CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:39]1[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 17998717HCID 17998717, compound

HCID 86700244HCID 86700244, compound

Product 1

HCID 86700246HCID 86700246, compound

Procedure

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid was prepared in a similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid except starting with 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride instead of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride. LCMS-ESI+: calc'd for C30H30ClN6O3S: 589.2 (M+H+); Found: 589.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 9.11 (s, 1H), 8.28 (d, J=5.4 Hz, 1H), 7.85 (s, 1H), 7.67 (dd, J=8.5, 1.7 Hz, 1H), 7.63-7.51 (m, 4H), 7.34 (d, J=5.3 Hz, 1H), 5.25 (s, 1H), 5.15 (s, 2H), 4.40 (t, J=5.3 Hz, 2H), 4.22 (t, J=5.4 Hz, 2H), 2.60 (s, 3H), 0.96 (s, 9H).

Sources & evidence

ORD record: ord-b36da237f4874269b15bd9285564c805
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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