Diisopropylethylamine → N-[(S)-1-(1-Cyanocyclopropylcarbamoyl)-3,3-difluoro-4-phenylbutyl]-8-azaspiro[4.5]decane-8-carboxamide

HRID 1913330ノート

反応式

HRID 1913330 の反応式
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:35][C:36]1([C:39]#[N:40])[CH2:38][CH2:37]1.[CH2:41]1[C:45]2([CH2:50][CH2:49][N:48]([C:51]([NH:53][C@@H:54]([CH2:58][C:59]([F:68])([F:67])[CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:55](O)=[O:56])=[O:52])[CH2:47][CH2:46]2)[CH2:44][CH2:43][CH2:42]1>CN(C=O)C>[C:39]([C:36]1([NH:35][C:55]([C@@H:54]([NH:53][C:51]([N:48]2[CH2:47][CH2:46][C:45]3([CH2:44][CH2:43][CH2:42][CH2:41]3)[CH2:50][CH2:49]2)=[O:52])[CH2:58][C:59]([F:67])([F:68])[CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:56])[CH2:38][CH2:37]1)#[N:40]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 66661164(S)-2-[(8-Azaspiro[4.5]decane-8-carbonyl)amino]-4,4-difluoro-5-phenylpentanoic acid

生成物 1

HCID 24996348N-[(S)-1-(1-Cyanocyclopropylcarbamoyl)-3,3-difluoro-4-phenylbutyl]-8-azaspiro[4.5]decane-8-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (331 μl, 252 mg, 1.95 mmol, 4 eq.), HATU (185 mg, 0.49 mmol, 1 eq.) and 1-aminocyclopropanecarbonitrile hydrochloride (58 mg, 0.49 mmol, 1 eq.) were added successively to a solution of the (S)-2-[(8-azaspiro[4.5]decane-8-carbonyl)amino]-4,4-difluoro-5-phenylpentanoic acid obtained as a crude product (192 mg, 0.49 mmol) in 10 ml of DMF. The reaction mixture was stirred at RT overnight and, the next day, concentrated under reduced pressure. The residue thus obtained was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA). The title compound was obtained in the form of a colorless crystalline material.

後処理

  1. concentrationthe next day, concentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA)

出典と根拠

ORDレコード
ord-e952f228e5064f4fa4dab3fa7009043a
出典データセット
uspto-grants-2013_12
特許番号
US08609681B2

反応ノート

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