Tetrahydrofuran → HCID 11678456, compound

HRID 1867618Notes

Reaction equation

HRID 1867618 reaction equation
[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].C(N(CC)CC)C.[OH:32][CH2:33][C:34]1[NH:35][C:36](=[O:45])[N:37]([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=1.[O:46]1CCC[CH2:47]1>>[OH:32][CH2:33][C:34]1[NH:35][C:36](=[O:45])[N:37]([CH:39]2[CH2:44][CH2:43][N:42]([C:47]([NH:1][C@@H:2]3[N:8]=[C:7]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:6]4[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=4[N:4]([CH2:19][C:20]([F:21])([F:23])[F:22])[C:3]3=[O:24])=[O:46])[CH2:41][CH2:40]2)[CH:38]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10854086HCID 10854086, compoundHCID 579795704-(Hydroxymethyl)-1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 11678456HCID 11678456, compound

Procedure

(3R)-3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (338 mg, 1.014 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (0.141 mL, 1.014 mmol) were added to a solution of p-nitrophenylchloroformate (204 mg, 1.014 mmol) in tetrahydrofuran (15 mL) at 0° C. After 1 h, 4-(hydroxymethyl)-1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one (200 mg, 1.014 mmol) was added and the reaction stirred at 0 oC for 10 min and was then heated to 50 oC. After 4 h, the reaction was partitioned between ethyl acetate and saturated sodium bicarbonate and the organics were washed with water, brine, and dried over magnesium sulfate. Purification by preparative reverse phase chromatography gave the title compound (18 mg). MS 557.21 (M+1).

Workup

  1. temperaturewas then heated to 50 oC
  2. waitAfter 4 h
  3. customthe reaction was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. washthe organics were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customPurification by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-aa8d35887aa64b8294c52f927146610a
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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