Hydrochloric Acid → (1S,2R,3S)-3-[6'-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3,4,5,6-tetrahydro-2H-1,2'-bipyridinyl-4-ylamino]cyclopentane-1,2-diol

HRID 2175100Notes

Reaction equation

HRID 2175100 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([OH:16])[C@@H:12]1[OH:17].[CH3:18][C:19]1([CH3:44])[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[C:25]2[CH:24]=[C:23]([C:31]3[N:36]=[C:35]([N:37]4[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]4)[CH:34]=[CH:33][CH:32]=3)[CH:22]=[CH:21][C:20]1=2.Cl>>[CH3:18][C:19]1([CH3:44])[CH2:28][CH2:27][C:26]([CH3:29])([CH3:30])[C:25]2[CH:24]=[C:23]([C:31]3[N:36]=[C:35]([N:37]4[CH2:42][CH2:41][CH:40]([NH:10][C@H:11]5[CH2:15][CH2:14][C@H:13]([OH:16])[C@@H:12]5[OH:17])[CH2:39][CH2:38]4)[CH:34]=[CH:33][CH:32]=3)[CH:22]=[CH:21][C:20]1=2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 672484016'-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3,5,6-tetrahydro-1,2'-bipyridinyl-4-oneHCID 67248684(1S,2R,3S)-3-aminocyclopentane-1,2-diol

Product 1

HCID 68380227(1S,2R,3S)-3-[6'-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3,4,5,6-tetrahydro-2H-1,2'-bipyridinyl-4-ylamino]cyclopentane-1,2-diol

Procedure

The preparation is carried out analogously to FS1007 without addition of DIPEA starting from 23 mg (0.199 mmol) of (1S,2R,3S)-3-aminocyclopentane-1,2-diol and 80 mg (0.199 mmol) of 6′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3,5,6-tetrahydro-1,2′-bipyridinyl-4-one. The product is in the form of the hydrochloride.

Sources & evidence

ORD record
ord-db6dc376f49743d096767f132df1a6a6
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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