HCID 86681096, compound → HCID 86681098, compound

HRID 1848125Notes

Reaction equation

C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:32]=[CH:31][C:19]4[N:20]=[C:21]([NH:23][C@@H:24]5[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]5[OH:30])[S:22][C:18]=4[CH:17]=3)[C:11]=2[CH:33]=1)(C)C.C[Si](C#CC1C=CC2N(CC3C=CC4N=C(N[C@@H]5CCCC[C@H]5O)SC=4C=3)C=NC=2C=1)(C)C>>[C:6]([C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:32]=[CH:31][C:19]4[N:20]=[C:21]([NH:23][C@@H:24]5[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]5[OH:30])[S:22][C:18]=4[CH:17]=3)[C:11]=2[CH:33]=1)#[CH:5]

Participants

Reactant 2

HCID 86681096HCID 86681096, compound

HCID 86681099HCID 86681099, compound

Product 1

HCID 86681098HCID 86681098, compound

Procedure

(1R,2R)-2-((6-((6-Ethynyl-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol was synthesized as a powder (7 mg, 18%) using a procedure analogous to that described in Step 2 of Example 121, substituting (1R,2R)-2-((6-((6-((trimethylsilyl)ethynyl)-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol from the previous step for (1R,2R)-2-((6-((5-((trimethylsilyl)ethynyl)-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol used in Example 121. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (s, 1H), 8.03 (d, J=7.2 Hz, 1H), 7.74 (s, 1H), 7.60-7.68 (m, 2H), 7.16-7.34 (m, 3H), 5.48 (s, 2H), 4.80 (d, J=4.0 Hz, 1H), 4.10 (s, 1H), 3.51 (m, 1H), 3.35 (m, 1H), 2.02 (m, 1H), 1.87 (m, 1H), 1.56-1.67 (m, 2H), 1.11-1.34 (m, 4H); LCMS (ESI) m/z 405 (M+H)+.

Sources & evidence

ORD record: ord-396c25113e0b4f83b2d2a84d769b1021
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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