Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 86636503, compound

HRID 913245Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)=[O:10])[CH:2]=1.[NH2:22][C:23]1[C:27]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:26][N:25]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:24]=1.C(N(C(C)C)CC)C.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(Cl)Cl>[C:31]([O:30][C:29]([NH:28][C:27]1[C:23]([NH:22][C:17]([C:16]2[CH:15]=[CH:14][C:13]([CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:21][CH:20]=2)=[O:19])=[N:24][N:25]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:26]=1)=[O:35])([CH3:34])([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4-({[(pyridin-3-ylmethoxy)carbonyl]amino}methyl)benzoic acid (0.1 g, 0.35 mmol), tert-butyl (3-amino-1-phenyl-1H-pyrazol-4-yl)carbamate (0.096 g, 0.35 mmol), and N,N-diethylisopropylamine (0.049 g, 0.35 mmol) in methylene chloride (5 mL) was treated with BOP (0.23 g, 0.52 mmol) and heated to 60° C. for 1 hour. The reaction was loaded directly onto a silica column and purified by flash chromatography (0-3% methanol/methylene chloride) to give pyridin-3-ylmethyl {4-[({4-[(tert-butoxycarbonyl)amino]-1-phenyl-1H-pyrazol-3-yl}amino)carbonyl]benzyl}carbamate as a white solid. 1H NMR (CD3OD) δ 8.57 (s, 1H), 8.48 (d, J=4.99 Hz, 1H), 8.38 (s, 1H), 7.97 (d, J=7.92 Hz, 2H), 7.87 (d, J=7.92 Hz, 1H), 7.72 (d, J=7.92 Hz, 2H), 7.44 (m, 5H), 7.27 (t, J=7.33 Hz, 1H), 5.18 (s, 2H), 4.38 (s, 2H), 1.50 (s, 9H).

Workup

custompurified by flash chromatography (0-3% methanol/methylene chloride)

Sources & evidence

ORD record: ord-51a149a75e444424a2c2937b828f30fe
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026260B2

Reaction notes

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