Pyrrole → HCID 21044361, compound

HRID 1837399Notes

Reaction equation

ClC(OCC)=O.N1C=CC=C1.[C:12]([O:16][C:17]([N:19]1[CH:23]([C:24]2[C:28]([NH2:29])=[C:27]([C:30]#[N:31])[N:26](C(OCC)=O)[CH:25]=2)[CH:22]2[O:37][C:38]([CH3:41])([CH3:40])[O:39][CH:21]2[CH:20]1[CH2:42][S:43][CH3:44])=[O:18])([CH3:15])([CH3:14])[CH3:13].N12CCCN=C1CCCCC2>>[C:12]([O:16][C:17]([N:19]1[CH:23]([C:24]2[C:28]([NH2:29])=[C:27]([C:30]#[N:31])[NH:26][CH:25]=2)[CH:22]2[O:37][C:38]([CH3:41])([CH3:40])[O:39][CH:21]2[CH:20]1[CH2:42][S:43][CH3:44])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

Reactant 4

HCID 8027Pyrrole

HCID 10928Ethyl chloroformate

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 69898274HCID 69898274, compound

Product 1

HCID 21044361HCID 21044361, compound

Procedure

The corresponding cyanomethylamino compound is then obtained by reaction, for example, with amino acctonitrile. This intermediate is then converted to the ester form by reaction with an esterification agent such as ethyl chloroformate. This intermediate is then cyclized to the corresponding pyrrol compound, 4-(4-amino-5-cyano-1-ethoxycarbonyl-1H-pyrrol-3-yl)-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester using, for example, 1,8-diazabicyclo[5.4.0]undec-7-ene. This compound was then converted to the corresponding amino derivative by removal of the ethoxycarbonyl substituent to produce 4-(4-amino-5-cyano-1H-pyrrol-3-yl)-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester. This compound, in turn was then reacted with formamidine acetate to form the target compound.

Workup

customThis compound was then converted to the corresponding amino derivative by removal of the ethoxycarbonyl substituent

Sources & evidence

ORD record: ord-f3c2bf0aef5945ac8fc9138383062917
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780993B1

Reaction notes

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