Benzofuran-2-carboxylic acid → HCID 67332297, compound

HRID 1672260Notes

Reaction equation

HRID 1672260 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:28]([O:32][C:33](=[O:60])[CH:34]([NH:44][C:45]([C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=2)=[CH:49][CH:48]=1)=[O:46])[CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([CH3:31])([CH3:30])[CH3:29].[O:61]1[C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=2[CH:63]=[C:62]1[C:70](O)=[O:71]>>[C:28]([O:32][C:33](=[O:60])[CH:34]([NH:44][C:45]([C:47]1[CH:48]=[CH:49][C:50]([C:53]2[CH:54]=[CH:55][C:56]([NH:59][C:70]([C:62]3[O:61][C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=4[CH:63]=3)=[O:71])=[CH:57][CH:58]=2)=[CH:51][CH:52]=1)=[O:46])[CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([CH3:29])([CH3:30])[CH3:31]

Participants

4

Reactant 3

HCID 10331Benzofuran-2-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67333061HCID 67333061, compound

Product 1

HCID 67332297HCID 67332297, compoundYield 40.1%

Procedure

BOP coupling of 2-[(4′-Amino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester (349 mg, 0.77 mmol) with 2-Benzofuran carboxylic acid (124 mg, 0.77 mmol, 1 equiv.) was carried out according to procedures in step A of Example 6B to give 185 mg of 2-({4′-[(Benzofuran-2-carbonyl)-amino]-biphenyl-4-carbonyl}-amino)-pentanedioic acid di-tert-butyl ester in 40% yield. MS (ESI) m/z 597.

Sources & evidence

ORD record
ord-14c7eae662ee4dfea3387a20ac1728b4
Source dataset
uspto-grants-2011_08
Patent number
US07998965B2

Reaction notes

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