N-(benzo[d]thiazol-2-yl)-2-(4-chloro-5-formylthiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide → HCID 178504249, compound

HRID 1518314Notes

Reaction equation

S1C2C=CC=CC=2N=C1N([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])C(C1C=CC=C2C=1CN(C1SC(Br)=C(C(OCC)=O)N=1)CC2)=O.[S:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[N:44]=[C:43]1[NH:51][C:52]([C:54]1[CH:55]=[CH:56][CH:57]=[C:58]2[C:63]=1[CH2:62][N:61]([C:64]1[S:65][C:66]([CH:70]=[O:71])=[C:67]([Cl:69])[N:68]=1)[CH2:60][CH2:59]2)=[O:53]>>[Cl:69][C:67]1[N:68]=[C:64]([N:61]2[CH2:60][CH2:59][C:58]3[C:63](=[C:54]([C:52](/[N:51]=[C:43]4/[S:42][C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=5[N:44]/4[CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:53])[CH:55]=[CH:56][CH:57]=3)[CH2:62]2)[S:65][C:66]=1[CH:70]=[O:71]

Participants

Reactant 2

HCID 59447544N-(benzo[d]thiazol-2-yl)-2-(4-chloro-5-formylthiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide

HCID 59447650ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-bromothiazole-4-carboxylate

Product 1

HCID 178504249HCID 178504249, compound

Procedure

Compound 45B was prepared in a similar manner to the synthesis of compound 34C by substituting compound 34B with compound 45A in step 3 of Example 34. Compound 45B was isolated as a white solid by trituration of the mixture of two isomers with 1:4 hexanes:EtOAc. The other isomer was isolated from the mother liquor: 1H NMR (DMSO-d6): δ 9.71 (s, 1H), 8.24 (d, J=7.82 Hz, 1H), 7.92 (d, J=7.58 Hz, 1H), 7.70 (d, J=8.06 Hz, 1H), 7.53-7.56 (m, 1H), 7.36-7.46 (m, 3H), 6.01 (s, 2H), 5.35 (s, 2H), 3.85 (t, J=5.92 Hz, 2H), 3.72-3.75 (m, 2H), 3.11 (t, J=6.04 Hz, 2H). MS (ESI(+)): m/z 585 (M+H).

Sources & evidence

ORD record: ord-6ae837d9a5f84686a66d8f4134998fe7
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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