Hydrochloric Acid → HCID 72549752, compound

HRID 626920Notes

Reaction equation

HRID 626920 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([C@H:18]2[CH2:22][CH2:21][C@:20]3([CH2:26][CH2:25][NH:24][C:23]3=[O:27])[N:19]2C(OC(C)(C)C)=O)[N:3]=1.CC1C=C(C2C=CC(C(F)(F)F)=CC=2)N=C([C@H]2CC[C@]3(CCNC3=O)N2)N=1.C(Cl)(Cl)[Cl:63].Cl>CCOCC>[ClH:63].[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)[N:5]=[C:4]([C@H:18]2[CH2:22][CH2:21][C@:20]3([CH2:26][CH2:25][NH:24][C:23]3=[O:27])[NH:19]2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 72549753HCID 72549753, compoundHCID 131735232HCID 131735232, compound

Product 1

HCID 72549752HCID 72549752, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a similar manner, tert-butyl (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (37 mg) was converted first to the free base (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]-nonan-6-one (27 mg); m/z 377 (M+H+); Optical Rotation α[D/20)]=+32.1 (c=0.56, CHCl3). This material was subsequently treated with HCl in ether to form (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride (E42) (32 mg); m/z 377 (M+H+).

Sources & evidence

ORD record
ord-a1b967c2e1f840639ba3ab3050becc96
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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