Glycine → (6-Amino-5-((5-phenoxy-thiophen-2-ylmethyl)-carbamoyl)-pyridin-2-ylamino)-acetic acid

HRID 2080199Notes

Reaction equation

[NH2:1][CH2:2][C:3]([OH:5])=[O:4].N12CCCN=C1CCCCC2.[NH2:17][C:18]1[N:39]=[C:38](Cl)[CH:37]=[CH:36][C:19]=1[C:20]([NH:22][CH2:23][C:24]1[S:25][C:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:27][CH:28]=1)=[O:21].C1C=CC(CC(NCN[C@H](C(O)=O)CC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1>CS(C)=O>[NH2:17][C:18]1[N:39]=[C:38]([NH:1][CH2:2][C:3]([OH:5])=[O:4])[CH:37]=[CH:36][C:19]=1[C:20](=[O:21])[NH:22][CH2:23][C:24]1[S:25][C:26]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 190 °C

Procedure

Glycine (610 mg, 8.13 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (405 μl, 2.71 mmol) were added to 2-amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (195 mg, 0.542 mmol) under nitrogen atmosphere, and the solution was stirred at 190° C. for 4 hours. Dimethylsulfoxide (5 mL) was added to the reaction mixture, which was then filtered with a polytetrafluoroethylene membrane filter (Whatman Inc), the filtrate was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), title compound (55.36 mg, 0.108 mmol, 20%) was obtained.

Workup

filtrationwas then filtered with a polytetrafluoroethylene membrane
filtrationfilter (Whatman Inc)
customthe filtrate was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record: ord-efe2b1a79dda49058f0ede8b0032f280
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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