Potassium Carbonate → (3R)-N-(4'-[(Isopropylamino)sulfonyl]biphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride

HRID 588348ノート

反応式

HRID 588348 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl.[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([C:16]([Cl:18])=[O:17])[CH2:9]2.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH:35][CH:36]([CH3:38])[CH3:37])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.O1CCOCC1>CN(C=O)C>[ClH:18].[CH:36]([NH:35][S:32]([C:29]1[CH:30]=[CH:31][C:26]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:16]([C@@H:10]3[CH:11]4[CH2:14][CH2:15][N:8]([CH2:13][CH2:12]4)[CH2:9]3)=[O:17])=[CH:25][CH:24]=2)=[CH:27][CH:28]=1)(=[O:34])=[O:33])([CH3:38])[CH3:37]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 57462844(3R)-Quinuclidine-3-carbonyl chloride hydrochlorideHCID 596940904'-Amino-N-isopropylbiphenyl-4-sulfonamide

生成物 1

HCID 11374690(3R)-N-(4'-[(Isopropylamino)sulfonyl]biphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

64.3 mg (0.46 mmol) of potassium carbonate are added to a mixture, prepared under argon, of 65.1 mg (0.31 mmol) of (3R)-quinuclidine-3-carbonyl chloride hydrochloride (Example 5A) and 45.0 mg (0.15 mmol) of 4′-amino-N-isopropylbiphenyl-4-sulfonamide (Example 12A) in 2.2 ml of a 10:1 mixture of dioxane and DMF. After 18 h at 100° C., the reaction mixture is concentrated in vacuo. The residue is dissolved in water and acetonitrile and purified by preparative HPLC. The product fractions are concentrated, mixed with 5 ml of a 2:1 mixture of acetonitrile and 1 N hydrochloric acid, again concentrated and dried under high vacuum. 21 mg (29.2% of theory) of the title compound are obtained.

後処理

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in water
  3. customacetonitrile and purified by preparative HPLC
  4. concentrationThe product fractions are concentrated
  5. additionmixed with 5 ml of a 2:1 mixture of acetonitrile and 1 N hydrochloric acid
  6. concentrationagain concentrated
  7. customdried under high vacuum

出典と根拠

ORDレコード
ord-29e0fb0e8f44421b84c79f09b029299b
出典データセット
uspto-grants-2016_01
特許番号
US09227964B2

反応ノート

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