Benzoyl chloride → HCID 178520224, compound

HRID 1349882Notes

Reaction equation

O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)=[N:8]1.[C:47](Cl)(=O)[C:48]1C=CC=[CH:50][CH:49]=1.C(N(CC)CC)C.[O:63]1[CH2:67][CH2:66][CH2:65][CH2:64]1>>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:45]=[CH:44][C:43]([NH:46][C:67](=[O:63])[CH2:66][C:65]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:64]=3)=[CH:42][CH:41]=2)=[N:17]1

Participants

Reactant 4

HCID 7412Benzoyl chloride

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 224801494-{1-Perhydro-2h-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]1h-indazol-3-yl}phenylamine

Product 1

HCID 178520224HCID 178520224, compoundYield 5%

Procedure

The title compound was prepared as described in Example 376, using 4-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.303 g, 0.50 mmol) in tetrahydrofuran (4.5 mL) was added benzoyl chloride (0.10 mL, 0.76 mmol) and triethylamine (0.35 mL, 2.52 mmol). The final crude product was purified by preparative HPLC (30–80% acetonitrile to H2O, 30 min.) (0.010 g, 5% yield): 1H NMR (DMSO-d6) δ 10.37 (s, 1H), 8.68 (br s, 1H), 8.07 (d, 1H), 7.95 (br s, 2H), 7.80 (d, 2H), 7.69 (br s, 1H), 7.30 (m, 5H), 3.69 (s, 2H); ES-MS (m/z) 395 [M+1]+.

Workup

customThe final crude product was purified by preparative HPLC (30–80% acetonitrile to H2O, 30 min.) (0.010 g, 5% yield)

Sources & evidence

ORD record: ord-52f86c3a4e55406787d01f5a6fc93be9
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211594B2

Reaction notes

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