Water → HCID 24770940, compound

HRID 1715305Notes

Reaction equation

[F:1][C:2]([F:35])([F:34])[C:3]1[CH:8]=[CH:7][C:6](C2(C3C=CC(NC(=O)CCC(O)=O)=CC=3)C=CON2)=[CH:5][C:4]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.CN(C)[CH2:39][CH2:40][CH2:41][N:42]=[C:43]=NCC.[OH:48][C:49]1[C:57]2N=N[NH:54][C:53]=2[CH:52]=[CH:51][CH:50]=1.[NH4+].[OH-:59].O.C(N([CH:67]([CH3:69])C)CC)(C)C.C[N:71]([CH:73]=[O:74])C>>[F:1][C:2]([F:34])([F:35])[C:3]1[CH:8]=[C:7]([C:53]2[CH:57]=[C:49]([C:50]3[CH:51]=[CH:52][C:43]([NH:42][C:41](=[O:59])[CH2:40][CH2:39][C:73]([NH2:71])=[O:74])=[CH:69][CH:67]=3)[O:48][N:54]=2)[CH:6]=[CH:5][C:4]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Reactant 7

HCID 962Water

HCID 6228Dimethylformamide

HCID 14923Ammonium Hydroxide

HCID 81531Diisopropylethylamine

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 68510123HCID 68510123, compound

HCID 178418300HCID 178418300, compound

Product 1

HCID 24770940HCID 24770940, compound

Procedure

The compound of Example 2 is dissolved in DMF and subsequently N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC.HCl; 1.5 eq), hydroxybenzotriazole (HOBt; 1.3 eq), NH4OH 25% in water (1.2 eq) and diisopropylethylamine (1.5 eq) are added. After 16 hours at room temperature the reaction mixture is concentrated and purified on silica gel (CH2Cl2/methanol 95/5→CH2Cl2/methanol/acetic acid50% 90/10/0.125 as mobile phase) resulting in pure title compound.

Workup

concentrationAfter 16 hours at room temperature the reaction mixture is concentrated
custompurified on silica gel (CH2Cl2/methanol 95/5→CH2Cl2/methanol/acetic acid50% 90/10/0.125 as mobile phase)

Sources & evidence

ORD record: ord-e428ff52c35b4ccea6737943d0600acc
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799812B2

Reaction notes

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