HCID 11743918, compound → HCID 10417779, compound

HRID 2113961Notes

Reaction equation

HRID 2113961 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([NH:6][C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[N:14]=2)=[C:10]([CH3:12])[N:11]=1)=[O:5].C1(=O)N([CH:37]([CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:60])[CH2:47][CH2:48][CH2:49][CH2:50][C@H:51]2[C@@H:59]3[C@@H:54]([NH:55][C:56]([NH:58]3)=[O:57])[CH2:53][S:52]2)[C:38]([O-])=[O:39])C(=O)CC1>CN(C=O)C>[CH3:12][C:10]1[N:11]=[C:7]([NH:6][C:4]([CH2:3][CH2:2][NH:1][C:38](=[O:39])[CH2:37][CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:60])[CH2:47][CH2:48][CH2:49][CH2:50][CH:51]2[CH:59]3[CH:54]([NH:55][C:56](=[O:57])[NH:58]3)[CH2:53][S:52]2)=[O:5])[S:8][C:9]=1[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:24][CH:25]=2)[N:14]=1

Participants

4

Reactant 2

HCID 11743918HCID 11743918, compoundHCID 77068325HCID 77068325, compound

Product 1

HCID 10417779HCID 10417779, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-N-{4-methyl-5-[2-(4-morpholin-4-yl-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-propionamide (75 mg, 0.17 mmol) in DMF (1 mL) was treated with succinimidyl-6-(biotinamido)hexanoate (32 mg, 0.085 mmol). After stirring at room temperature for 3 h, the reaction mixture was purified by preparative RP-HPLC (0-60% MeCN in 0.1% aq CF3COOH over 40 min, 9 mL/min) to afford the title compound as an orange solid. Anal. RP-HPLC: tR=13.2 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity>97%). MS (ESI+) m/z 776 (C37H50N10O5S2 requires 778.9).

Workup

  1. customthe reaction mixture was purified by preparative RP-HPLC (0-60% MeCN in 0.1% aq CF3COOH over 40 min, 9 mL/min)

Sources & evidence

ORD record
ord-331e3ba4308e487aa6843b72485c2da2
Source dataset
uspto-grants-2008_10
Patent number
US07432260B2

Reaction notes

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