Hydrochloric Acid → HCID 131723703, compound

HRID 2298104Notes

Reaction equation

HRID 2298104 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][CH:13]([NH:16]C(OC(C)(C)C)=O)[CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[C:37]12([CH2:47][CH2:48][NH2:49])[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2.C(N(CC)C(C)C)(C)C.Cl>O1CCOCC1.CO.CN(C)C=O>[ClH:1].[NH2:16][CH:13]1[CH2:14][CH2:15][N:11]([C:8]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([CH:7]=2)[C:4]([NH:49][CH2:48][CH2:47][C:37]23[CH2:46][CH:41]4[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]4)[CH2:38]2)[CH2:44]3)=[O:6])[CH2:12]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27711382-(Adamantan-1-yl)ethan-1-amine hydrochlorideHCID 53742797HCID 53742797, compound

Product 1

HCID 131723703HCID 131723703, compoundYield 43.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared as described in example 74 above using (+/−)-2-chloro-5-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-benzoic acid (0.090 g), 1,1′-carbonyldiimidazole (0.043 g), tricyclo[3.3.1.13,7]decane-1-ethanamine, hydrochloride salt (0.057 g), N,N-diisopropylethylamine (0.046 ml) and dimethylformamide (3 ml). This compound was treated with 4N hydrochloric acid in dioxane (0.5 ml) and methanol (5 ml) to yield the title compound (0.025 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5e3c9e4b3ee042d898588752e5c124fe
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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