Diisopropylethylamine → HCID 12073337, compound

HRID 1369053Notes

Reaction equation

HRID 1369053 reaction equation
[CH2:1]([N:8]([C@@H:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][C@H:28]1[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:9]([CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24](O)=[O:25])[CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:44][C:45]1[CH:50]=[CH:49][C:48]([S:51]([NH2:54])(=[O:53])=[O:52])=[CH:47][CH:46]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:1]([N:8]([C@@H:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][C@H:28]1[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:9](=[O:10])[CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([NH:54][S:51]([C:48]3[CH:47]=[CH:46][C:45]([F:44])=[CH:50][CH:49]=3)(=[O:52])=[O:53])=[O:25])[CH:19]=2)[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1202314-FluorobenzenesulfonamideHCID 2733179PyBroPHCID 70011715HCID 70011715, compound

Product 1

HCID 12073337HCID 12073337, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 1 (82.0 mg, 0.145 mmol), 4-fluorobenzene sulfonamide (27.9 mg, 0.160 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBroP, 74.4 mg, 0.160 mmol), and methylene chloride (12 mL) was added diisopropylethyl amine (0.126 mL, 0.725 mmol). After stirring for 5 h, the reaction was concentrated to dryness and then diluted with ethyl acetate (25 mL). This was then washed with 0.1 N HCl (2×20 mL) and brine (25 mL), dried (magnesium sulfate), and concentrated. The title compound was isolated in quantitative yield as a foam following chromatography on silica gel with ethyl acetate/hexane.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. additiondiluted with ethyl acetate (25 mL)
  3. washThis was then washed with 0.1 N HCl (2×20 mL) and brine (25 mL)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-90eb4b7bd73448deb13d44a7d57bf3f2
Source dataset
uspto-grants-2003_06
Patent number
US06576632B1

Reaction notes

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